From the Litchfield Hills to Mystic Country; Greenwich to Stonington: the best shops, restaurants, attractions, and activities to explore across Connecticut on your next getaway
Welcome to the Gateway to New England
That's actually the tagline for my hometown of Greenwich. But it applies to the entire state.
Connecticut is the first state most visitors enter when traveling to New England from anywhere else in America.
And there's as much diversity here in our little state as you'll find in the rest of our region:
And all easily accessible year-round.
Skip the tedium of researching for your next getaway to Connecticut by reading this guide:
You'll find that and much more in abundance here in Connecticut.
Colin Pearson
Colin Pearson
(Innkeeper at Stanton House Inn in Greenwich, Connecticut)
22 of the most cute towns in Connecticut
Quaint, charming, and adorable is how we'd describe our favorite cute towns in Connecticut; from Greenwich to Stonington to Cornwall.
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In fact, with few exceptions, most of the 169 towns that make up Connecticut have their cute or funky sides.
Exploring all the various towns in our small state would take more than the average visitor would expect.
There are plenty of ways to prioritize exploring towns, a few that come to mind include visiting points along:
Or just plan CT day trips throughout corners of the state.
Any time of the year is a perfect time to visit cute towns in CT, as each season packs a different experience.
Read on for our list of our favorite cute towns in Connecticut.
We broke-down our list by county, but don’t let that intimidate you. No point in the state is more than an hour and a half to two hours away from anywhere else.
The closest county to New York City, Fairfield County changed over the years. At first a largely rural area, it changed to bedroom communities of the nearby metropolis. With an easy commute back to the City, it’s no wonder that these cute Connecticut towns close to NYC are home to many New Yorkers.
But the area is now a destination in its own right.
In fact, there’s plenty of overlap between some of the top Fairfield county destinations and our list of cute towns.
Just 40 minutes by train from Grand Central Terminal, Greenwich is a perfect, quick getaway from the frenetic life of the City.
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The town is more of a collection of distinct neighborhoods that are cute towns in their own right. Each of these neighborhoods have their own feel, for example:
But each features gorgeous historic buildings and quaint museums and local points of interest. Each neighborhood also has fantastic parks and hiking trails. While each neighborhood used to have their own charming local inn, most have closed in recent years. Our downtown Greenwich bed and breakfast is the last remaining one in town.
Greenwich has more of a cosmopolitan feel than other cute towns in CT, so you wouldn’t realize that it’s one of the oldest towns in the state. English settlers founded the town in 1640 to limit the advance of Dutch settlers up the Long Island Sound from Manhattan.
Today, downtown Greenwich and the shopping district centered around Greenwich Avenue, our main street, is a major shopping destination for the Tri-State area. Avid shoppers are sure to enjoy the mix of major brand names and designer boutiques as well as some of the more quirky independent shops, holdovers from Greenwich’s less high-end days.
Plan a visit to our hometown with our Visitors Guide to Greenwich, Connecticut.
Thanks to advanced foresight and good geography, Westport has been named one of the best beach towns in the entire country.
But one of the major local attractions isn’t actually owned by the town. Back in 1914, when Westport was just a farming community, State Park Commission official Albert Turner picked Sherwood Island for a park. It took the state 23 years to acquire the necessary land from reluctant owners. But in 1937, Sherwood Island State Park finally opened.
Today, it’s one of the best beaches near Greenwich, Connecticut, and ensures that Westport’s fantastic beachfront remains open to all, regardless of development.
And Westport does have some of the most expensive real estate in the state. But it’s easy to see why the real estate market is so brisk here.
Downtown Westport offers great shopping and fantastic restaurants along the Saugatuck River. And the separate seafront area features a row of gorgeous brick buildings, the sight of which is particularly striking at sunset. And you’ll find old fashioned board houses dating back to colonial times, palatial mansions, and beautiful, large parks all throughout town.
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The arts scene in Westport is strong, too, with Westport Country Playhouse for theatre and the Westport Arts Center for visual and performing arts.
Inland from Westport, Ridgefield, Connecticut, packs a cultural punch.
After exploring some of the best hiking trails in Connecticut at Devil’s Den Preserve, head to Weir Farm National Historic Park. There, you’ll find America’s only National Park for Art in Impressionist J. Alden Weir’s home, which he called, “The Good Place”.
Afterwards, head to Ridgefield Center and the Aldrich Museum of Contemporary Art. Contemporary artists just starting out display their works in this revamped 18th century building.
If you want to learn more about Ridgefield’s 300 years of history, including a famous Revolutionary War battle fought here, walk the historic Museum in the Streets trail in the center of town. You can also explore the historic Keeler Tavern Museum.
Personally, I only equate Monroe, Connecticut, with Benedict’s, the closest farm store to Greenwich. I head there whenever I get any sort of agrarian impulse, be it gardening or chicken keeping. It’s fun to poke around, though, not only for the livestock they keep there, but now for the new walking trail they’ve named, “The Cow’s Path”.
But Monroe is also known for its history. Monroe was named after James Monroe, America’s fifth President. And its historic district looks straight out of Connecticut’s colonial period.
There are plenty of parks, plus hiking and cycling trails to keep you busy here. The William E Wolfe Park and Webb Mountain Park, with a scenic view of the Housatonic, are worth a visit.
If you’re looking for more to fill your afternoon once you’re done, hop over to Shelton and check out Jones Family Farms and the waterfall and brook at Indian Well State Park.
The various small towns of Litchfield County in northwest Connecticut are the destination for many travelers in the Fall. There are various beautiful CT fall foliage driving routes leading up to or around the area.
But anytime of year is a good time to visit Litchfield County.
Cross the Housatonic River from the Danbury area of Fairfield County and enter into classic New Milford.
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The Weantinock, a tribal subgroup of the Paugusset Native American tribe, lived, farmed, and fished here for centuries before John Noble arrived.
But he did in 1707, when he settled a small community named after Milford on the coast.
Come to New Milford early on a Sunday morning, so you can start your day at the Elephant’s Trunk, the largest flea market in New England.
If you haven’t filled-up your car with flea market finds, drive to Lovers Leap State Park. According to legend, local Pootatuck Chief Waramaug’s daughter, Princess Lillinonah, leapt to her death with her lover, hence the name.
Today, the park’s hiking trails offer scenic views of the Housatonic and visits to century-old industrial ruins.
Afterwards, be sure to visit the center of New Milford. Visit the Village Center for the Arts, and be sure to walk around the quaint and spacious town green. Walk down to the river to enjoy the gorgeous views along the New Milford River Trail.
Continue to follow Route 7 northwards along the Housatonic River to reach Kent, Connecticut.
Little, funky Kent has been designated a top foliage town in the entirety of New England.
Founded originally for the production of iron, the town is home to a historic covered bridge, Bulls Bridge. It’s also the location of Kent Falls State Park, which contains no fewer than 17 waterfalls.
But that’s not the only park to explore here. Macedonia Brook State Park has hilltops along its hiking trails that look onto the Catskill and Taconic Mountains. There are some amazing views at the Western New England Greenway and East Kent Hamlet Land Trust.
And if you feel like saying you hiked a piece of the Appalachian Trail, head to the nearby Schaghticoke Reservation.
But the center of town is a major draw for New Yorkers, full of charming boutiques, antique shops, and artsy cafes. You can also learn more about the history of the area at the Kent Historical Society or Sloane Stanley Museum and Kent Furnace.
Continue north on Route 7 from Kent to reach even smaller Cornwall, Connecticut.
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The local poet, Mark Van Doren, loved the town so much that he wrote “Hills of Little Cornwall”. His poem describes the idyllic natural beauty of the countryside surrounding the town.
Cornwall is most famous for its covered bridge, which is prettier than Kent’s, in this writer’s humble opinion. Built of timber in 1762, the bridge makes a great entrance to town.
And the little town is a cluster of what look like quaint gingerbread houses, perched on the hill rising from the Housatonic River.
As you head out of town to the southeast, be sure to check out Mohawk State Forest. Local Tunxis and Paugussett tribes used smoke signals from the height of Mohawk Mountain to warn of approaching Mohawk attacks from the northwest, hence the name. Today, the hiking trails offer a chance to see a rare black spruce bog or a spectacular view of the area from the top of the mountain.
You can also head here in the winter to ski at Mohawk Mountain.
Southeast of Cornwall is the former county seat, Litchfield, Connecticut.
White Flower Farm is known by gardeners across the country, and hosts ten acres of display gardens to enjoy.
At 4,000 acres, White Memorial Foundation is the state’s largest nature center and wildlife sanctuary with 35 miles of trails.
Continue southwest of Litchfield to reach the tiny town of New Preston.
Blink and you might miss this little town on the shores of Lake Waramaug. But you would be much poorer for it, as Lake Waramaug is one of the most beautiful lakes in Connecticut.
There are a few shops to peruse in this tiny town perched above a waterfall, as well as a restaurant or two. The Hopkins Inn has been hosting guests since 1847, and a glass of wine at Hopkins Vineyard is a great way to wile away some time on a sunny afternoon.
A beautiful Sunday afternoon in and of itself is to walk or bike the 8-mile loop around Lake Waramaug, with a stop at Hopkins Vineyard to refresh the spirits.
New Preston is just a borough of the larger (but still small) Washington, Connecticut.
But Washington was the inspiration for the town of Stars Hollow of the show, Gilmore Girls.
Enjoy a flat trail along the river’s edge of Steep Rock Preserve, or climb the hills and find the old abandoned railroad tunnel. Hidden Valley Preserve and Maricosta’s Preserve are worth hiking, as well.
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Head to the Institute for American Indian Studies to learn more about the Native American influence in the area. The Gunn Historical Museum preserves American artifacts and stories from the area, while the Hollister House occupies 25 acres of private gardens filled with whimsical, unique water features and Japanese accents. The Washington Art Association and Gallery in picturesque Washington Depot offers art classes as well as shows and art sales.
If you were theoretically visiting all these towns on one long driving loop, you would drive back down to Fairfield County and continue east along the Connecticut shoreline.
Once you cross the Housatonic River, you’ll be in New Haven County and the first town on this list, Milford.
The view of Milford from I-95 is misleading: strip malls galore line the Post Road in Milford, Connecticut.
But get off the highway and drive to Old Town Milford for a far more pleasant locale: streets lined with historic buildings, quaint cafes, boutiques, and funky bookshops. Milford’s town green is the second largest one in New England, with its own pond, streams, and even a small island.
But Milford is also known as a beach town. Walnut Beach has one of the longest boardwalks in the state, while Silver Sands State Park’s 297 acres are full of dunes and marshes along Long Island Sound.
Skip past New Haven to get to the next cute town to the east of the city, Branford.
Branford has the largest piece of the so-far completed Shoreline Greenway Trail, which will eventually follow the Connecticut Shoreline from New Haven to Madison.
The cutest section of Branford is Stony Creek. This tiny beach community has everything in a micro-scale: tiny houses, a tiny community beach (Stony Creek Beach), and even a tiny combination gift shop and market that serves as a local breakfast and deli spot, plus pizzeria in the evening.
But Branford is also the site of one of the most unique attractions in all of Connecticut: the Thimble Islands. This chain of about 25 small, rocky and wooded islands feature summer cottages built in the Victorian era. While getting on them is trespassing, you can take a Thimble Islands Ferry Cruise and get a tour of the islands, plus their history.
Just to the east of Branford is Guilford, Connecticut.
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One of the oldest towns in Connecticut (but not older than Greenwich), Guilford offers free guided walking tours to learn more about its 375 years of history.
Bishop’s Orchards Farm Market and the various fruit-picking orchards are a major draw in the warm months. The sprawling orchards are some of the best apple orchards in Connecticut.
Two waterfront locations to breathe the salty air in this Connecticut beach town are Chaffinch Island and Jacob’s Beach.
The Place Restaurant is one of the more unique dining establishments in Connecticut. This seasonal restaurant features tree stump chairs and bright red tables. The seafood is cooked over an 18 foot fire pit–plan to have the roasted lobster, if you’re not allergic.
If you’re not tired of getting gobsmacked by history, the Whitfield House, built in 1639, is the oldest house in Connecticut, and the oldest stone house in all of New England. The Henry Whitfield State Museum, centered on the Whitfield House, offers a look at the lifestyle and culture of colonial America.
Cute, beachy, Madison was first settled in 1641.
Just east of Guilford, the biggest draw to Madison is the sweeping Hammonasset Beach State park and Meigs Point Nature Center. But Madison’s portion of the Shoreline Greenway Trail is quite pleasant, as well.
Madison’s downtown offers some unique shops, like the Audubon Shop, R.J. Julia Booksellers, and the Madison Art Cinema.
Three Connecticut counties down, three to go!
Middlesex gets its name from a region in England, meaning territory of the middle Saxons. It has nothing to do with what some teenagers assume.
This cute town on the Connecticut River is one of the few to be attacked by a foreign country.
British vessels commandeered the town during the War of 1812. While there were no casualties, British looting left the town severely damaged.
But fortunately, the town rebounded to a state which made another source of inspiration for Stars Hollow of The Gilmore Girls.
The town of Essex, perched on a peninsula, hosts:
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The Essex Steam Train pulls vintage train cars along the Connecticut River from here. It’s also the site of the Griswold Inn, one of the oldest continuously operating inns in the entire country.
Pop over to the Connecticut River Museum for sweeping views of the river. Or head to Scott’s Farm & Greenhouses from mid-July until the end of the season for pick-your-own flowers, sold by the pound.
A northward drive along Connecticut’s route 9 from Essex brings you to Chester.
This unassuming little town on the banks of the Connecticut River began as a small industrial center. The major sources of employment in-town were shipbuilding and milling.
Today, the quaint downtown streets are a major draw.
Antique houses and the architecture in the central part of town have been well-preserved to the present day. The art galleries, boutiques, and local theatre are draws as well.
Heading further out of town, Chester offers hiking trails to explore its bucolic scenery.
And if you’re ready to visit one of the most unique attractions in Connecticut, take the Chester/Hadlyme Ferry across the river to East Haddam.
There, you can visit Gillette Castle State Park. As the name suggests, William Gillette, an eccentric actor famous for playing Sherlock Holmes, paid for what looks like a medieval fortress overlooking the Connecticut River.
At the mouth of the Connecticut River sits Old Saybrook. Founded in 1635, it’s one of the oldest towns in the state, beating Greenwich by 5 years.
The Old Saybrook Fort controlled the main trade and supply route to the Connecticut River Valley and the interior of New England. As such, this town was strategically important for centuries.
The Collegiate College of Connecticut was first chartered in Old Saybrook. But the school later moved to New Haven and was renamed Yale University after a generous donation from a merchant of that name.
More recently, this was the favorite haunt of actress Katharine Hepburn, who lived on the outskirts of town. The Katharine Hepburn Cultural Arts Center in town has an active list of events focused on performances, music, and theater.
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As befits an old town, Old Saybrook’s history includes a few more firsts, like the first soda fountain installed in 1896.
Old Saybrook’s Main Street includes numerous independent, family-owned shops housed in quaint old storefronts. Further out of town, you’ll find many historic manor houses, and the Old Saybrook Lighthouse, also known as Lynde Point Light.
Snap a picture or two of the Amtrak Old Saybrook-Old Lyme Bridge, then hop on I-95 northbound to cross the Connecticut River into New London County.
New London County hugs the Connecticut shoreline from the Connecticut River to the Rhode Island border.
This is the area Connecticutians equate with coastal Connecticut: yachts, more modest sailboats, seafood, cute little farms, and quaint whaling towns.
Nestled into a corner of the town of East Lyme is the seaside resort village of Niantic.
It was named after the Niantic People, a tribe that inhabited the area long before the arrival of Europeans.
Start in the center of town, where you’ll find a variety of unique and funky shops. The Book Barn is a bookstore of over 350,000 titles, including out of print and rare books. Three Belles Outfitters, meanwhile, is the largest hobby kayak store on the East Coast.
But the beaches here are a major draw, of course. Rocky Neck State Park is close by with plenty of parking and access. Which is good, because little McCook Point Beach and Park are beautiful, but tiny. The views of the harbor from the bluff of the park are lovely, though.
From Hole-in-the-Wall Beach, walk along the Niantic Bay Boardwalk and enjoy the view of the harbor.
Niantic is also the place to go to book deep water fishing charters from Connecticut. Some of the top deep water fishing charter companies include:
A beautiful place to stay in Niantic, overlooking the harbor yet still close to town, is the Inn at Harbor Hill Marina.
Everyone and their mother has heard of Mystic, Connecticut.
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The name of the town was derived from the Native American term, “missi-tuk”. The word describes a large river whose waters are driven into waves by tides or wind.
It was originally one of Connecticut’s most important seaports. More than 600 vessels were constructed along the shores of the Mystic River between 1784 and 1919.
Today, it is the state’s most popular tourist destination. It’s like Connecticut’s version of Myrtle Beach, except way less tacky.
Mystic Seaport started first, to honor the area’s maritime history. It is one of the country’s largest maritime museums, with a collection of four historic ships and merchant vessels. The most famous of the ships is the Charles W Morgan whaling ship.
Then they threw-in the Mystic Aquarium, and how could you not spend a day or two here? They have beluga whales and sea lions!
But this little coastal town (that isn’t actually a town, it’s a village split between Groton and Stonington) has more to attract the tourists than just those two mystical attractions.
Badumpsh.
Colonial period houses line Mystic’s Main Street. And the abundance of quaint shops and restaurants should keep you busy for a while.
Mystic and the area is known for its seafood, but there are a couple other shops that require a closer look:
Some other cool nearby attractions include:
If you’re interested in staying a few days, the Whaler’s Inn is right in the heart of Mystic. For something with more of a country feel, check out Stonecroft Country Inn in Ledyard, Connecticut.
The Village, as it’s called locally, is unlike any other place in Connecticut.
This little old whaling town, huddled together on a small, windswept peninsula, is well-worth a visit for a quieter afternoon than you’ll find in nearby Mystic.
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Someone once wrote that it’s as if a piece of Nantucket somehow separated itself and floated down to this corner of southeastern Connecticut.
The mansions of varying architectural styles clustered together on the narrow streets are reminiscent of some of the other major historic attractions on the East Coast, like Annapolis or Charleston.
Away from the historic center but still in Stonington, you’ll find more to entertain. Some of the best Connecticut wineries on the Connecticut Wine Trail are here:
Some hold-outs from an older time remain here, as well. Connecticut’s last remaining fishing boat fleet sails out of Stonington, for example. And the oldest steam-powered cider mill in America is still operating at Clyde’s Cider Mill.
Exhausted by this trip around the state to find Connecticut’s cutest towns yet?
Neither are we, promise.
The last county to visit on our list is centered around Hartford, the state capitol. Since you’re looking for cute towns, you can easily skip Hartford on this specific road trip.
Instead, start just south of Hartford in Wethersfield, Connecticut.
Founded in 1634, Wethersfield claims to be the oldest town in Connecticut. Windsor also claims that title, as Pilgrims established a trading post there in 1633. Who you side with depends on what you consider settlement: people trading in a spot, or people actually calling a location home.
Or you’ll side with whichever town is cuter.
Regardless, Wethersfield’s historic district has over a thousand buildings dating from the 17th, 18th, and 19th centuries. Three buildings are even listed on the National Register of Historic Places, all fantastic examples of Colonial architecture:
Fishing and boating enthusiasts will likely elect to skip the historic houses and head to Wethersfield Cove.
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For a place to stay in Wethersfield that will make you feel like you’re staying in the town’s heyday, be sure to visit the Silas W Robbins House.
Head up into the hills of Hartford County to find the last cute town on the list, Simsbury.
Start just on the outskirts of town at the Drake Hill Flower Bridge. This Parker truss railroad bridge was decommissioned and covered with pots of vibrant plants across the Farmington River.
From there, walk into downtown Simsbury. Be sure to check out the Simsbury Art Trail, a collection of John Seward’s sculptures, that line the main thoroughfares.
If a more active trail is your preference, you can also take your bike along the Farmington River Trail stretching from West Suffield to Southington.
But one of the most famous attractions in Simsbury, and one of the best places to witness Connecticut fall foliage, is the Heublein tower in Talcott Mountain State Park. In the entire state, the view and eccentric, Bavarian-looking castle make this one of this writer’s favorite hiking trails in CT.
Overwhelmed?
So are we.
But we’ve completed our armchair tour of cute towns in Connecticut!
A few more common questions from visitors to Connecticut include:
In no particular order, that would be:
Many of the towns on this list are mentioned above, but a few didn’t make the cut because they weren’t cute enough, or too big, or too pretentious to be considered cute.
Not saying who.
But the most artsy and funky towns in Connecticut include:
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I might be a bit biased, but the Fall in Connecticut is amazing. There’s a reason the tourists visit from New York and Boston during Autumn.
But each season has its own special appeal. And each town will feel completely different depending on the season.
While everyone knows summer in a Connecticut shoreline resort town is delightful, winter in Connecticut is cozy, quaint, and classically New England.
From Mystic to Greenwich, find the most quirky, funky, or simply unique things to do across Connecticut, including unique dining and events.
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16 of the most unique things to do in Connecticut
Of the lengthy list of CT activities, what are the most unique?
As in, what are ones you would have a hard time experiencing somewhere else?
Stretching from Greenwich in the west to Stonington in the east, below are our picks for the most unique things to do in Connecticut.
While other places make a to-do about horse racing, no one enjoys the Sport of Kings quite like Greenwich.
The Greenwich Polo Club hosts matches on Sundays. These are as delightful affairs as those much better known horse-focused sporting events.
You’ll likely bump into a celebrity or two while taking part in the time-honored tradition of stomping divots in the field. The experience certainly makes for one of the most unique date ideas in Connecticut.
Prince Harry has played a match here, and many more of the rich and famous have enjoyed an afternoon picnic during a match.
As befits an unstuffy yet luxurious affair, be sure to bring a picnic of at minimum a bottle of champagne and cheese spread.
And definitely a polo shirt.
This 37-mile parkway through the backwoods of southern Connecticut is a historic gem.
The Merritt Parkway was built before I-95 to help lower traffic volumes on the Post Road. My mother has memories of her parents going for relaxed Sunday drives on the Merritt Parkway, stopping to picnic on a shoulder along the way.
Today, it’s quite a bit more crowded. And yet trucks and commercial vehicles are banned due to the low height of the historic bridges crossing the parkway.
The bridges themselves are a draw. Each one was individually designed to represent architectural styles popular in the 1930s:
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The Merritt Parkway is also the site of the nation’s first clover leaf entrance and exit ramps. And the service areas were recently renovated for drivers needing a Dunkin’ Donuts fix.
Bring your hiking boots on your trip, if you’re so inclined. Some of the best hiking trails in Connecticut are scattered along the route of the Merritt.
Shortly before the Parkway ends after crossing the Housatonic River, you’ll find a small museum in Stratford devoted to the design and construction of this bucolic holdever through Fairfield County.
Philip Johnson was an American architect born in Ohio who settled in New Canaan, Connecticut. While his stature has diminished of late, he is considered one of the most influential 20th century architects.
Mr Johnson designed Abby Aldrich Rockefeller Sculpture Garden at the Museum of Modern Art and the former Four Seasons restaurant.
And one of the most famous of his works is only a 25-minute drive from downtown Greenwich, in New Canaan.
Built over 37 years on 49 acres, Philip Johnson turned homebuilding on its head with The Glass House. Instead of dividing a single interior into rooms, he divided the space into 14 structures, each with a different function, for example:
One of the most famous quirks of the house is that almost the entire structure is one room. Only the bathroom features enclosed and opaque walls.
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Otherwise, the home is around 2,000 feet of open space with only floor-to-ceiling glass and the steel to hold the panels in place around the entire exterior. Johnson famously joked that he had the most beautiful and expensive wallpaper the world had ever known.
Johnson completed his home in 1949. He also designed such quirks as a brick guesthouse with no windows, an edgeless gatehouse called “Da Monsta”, and an underground art gallery styled after Agamemnon’s tomb.
He famously quipped that Architecture is the art of how to waste a space.
And perhaps he was thinking of the Glass House when he made that comment. While Johnson lived here for parts of his life, it eventually became just a space for entertaining.
After all, floor-to-ceiling glass doesn’t afford much privacy.
It’s now a certified National Trust Historic Site, open May 1 to November 30.
From the bustling downtown of South Norwalk, ride the ferry from May to September out to Sheffield Island.
The island offers beaches, beautiful views of Norwalk harbor, waterside trails through the island’s wildlife refuge, and ample space for picnicking.
But the main draw is the Sheffield Island Lighthouse. Built in 1868, the lighthouse was in operation until 1902. Today, you can enjoy a tour of this historic site, and see sweeping views of Long Island Sound, and even the NYC skyline on a clear day.
But there are historic lighthouses up and down the East Coast, right?
There’s something more that’s unique to the area that happens here every Thursday evening from June to September.
One of the most unique and well-known displays of New England cuisine is the clambake.
A clambake is a traditional, New England, method of cooking seafood using seaweed to steam the quahogs, clams, lobsters, mussels, et cetera.
Order tickets for the Thursday evening clambake to enjoy:
But the main attraction is the clambake, of course. A multi-course meal featuring corn on the cob, potatoes, clams, salad, and dessert are all served under a tented pavilion on the lighthouse lawn.
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Be sure to bring your own beverages (including beer or wine), and plenty of bug spray.
Nestled off the beaten path in Wilton, Connecticut, sits one of only two national historic sites devoted to the visual arts.
In 1882, Impressionist painter J. Alden Weir, established himself, his work, and his family at Weir Farm. Three generations of painters would follow until the site became a national historic site in 2005.
Visitors can explore the hiking trails through the former fields of the farm, take a tour of the Weir studio and home, and even paint their own masterpiece.
With the grounds of Weir Farm open year-round, it’s one of the best free things to do in Connecticut.
P.T. Barnum of circus fame was born in Bethel, Connecticut, but loved Bridgeport.
It’s where he spent much of his life, and even served as its mayor for a time.
And when he died and was buried there, he bequeathed much of his most unique treasures to the city.
In downtown Bridgeport, close to I-95, sits a unique red and yellow domed building made of stone and terracotta. Barnum designed the three-story building himself, intending it to be an institute for science and history.
Some of the oddities of the P. T. Barnum Museum’s collection includes:
After suffering some severe damage from a recent hurricane, the main building is closed, though some of the museum’s items are on display next door.
One of the oldest universities in America sits in downtown New Haven, Connecticut.
But there’s plenty of things to do here, even if you’re not an alum.
Visitors to Yale University can walk the campus grounds, whose Gothic style, inspired by Cambridge and Oxford universities, are reminiscent of Hogwarts to some modern visitors.
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Visit the world-class (and many of them free) museums on campus. Some of the most popular Yale museums include:
Afterwards, be sure to take the free daily tour of campus led by current Yale students.
As far as historic attractions focused on the performing arts goes, much of the attention goes to the Goodspeed Opera House.
But the smaller, unassuming Ivoryton Playhouse is just as unique, and with an interesting cultural history.
Built in 1911, this theatre is the oldest continuously performing summer theatre in the United States. And it’s been self-supporting for the entirety of its history.
A few of the famous names that have made appearances at Ivoryton Playhouse include:
In non-pandemic periods, the troupe produces award winning comedies, dramas, and musicals throughout the year.
Connecticut is all about quaint and appreciating the history of the state.
And one of the most quaint and historical experiences is riding along the Connecticut River by train and boat.
The only remaining steam train and riverboat connection in America is based in Essex, Connecticut, as the name implies. Navigators meet at the historic 1892 Essex train station to start their excursion.
Then, spend 2 and a half hours on a narrated trip up the Connecticut River Valley, seeing such sights along the way as Gillette Castle and the Goodspeed Opera House.
Visitors can add extra activities to their trip with the Essex Steam Train, such as a dinner train service, or hiking excursion to Gillette Castle.
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Any time of year can be an appealing time to take this trip, as the 30 miles or so of the river from the mouth up to Middletown is picturesque villages and marshes. It’s why The Nature Conservancy deemed the Connecticut River Valley one of “the last great places on Earth”.
Having explored much of Connecticut, another category of attraction that stands out is quirky eccentricities created by excess wealth.
An early 19th century example of that eccentricity is Gillette Castle.
William Hooker Gillette is best known for his portrayal of Sherlock Holmes. The original actor of this character introduced such iconic props as:
He was even the source of the phrase, “Elementary, my dear Watson.”
But his 1919 home is an attribute to a rather odd gentleman. The 24-room mansion looks like a medieval stronghold from the outside, but the eccentricities certainly don’t stop there.
Some of the oddities that Gillette designed himself include:
Start your visit with a grand entrance by taking the Hadlyme ferry across the Connecticut River from Chester. From spring to fall, you’ll be sure to enjoy the beautiful views on your approach to the castle and state park.
Revenue from the Indian Casinos like Foxwoods Resort Casino has funded some amazing institutions.
One of which is the Mashantucket Pequot Museum & Research Center, the largest Native American museum in the world.
This museum is a tribally owned complex documenting Native American and the natural history of Southern New England. The impressive collection is nestled in an ancient cedar forest close to Foxwoods.
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The museum uses text panels, films, and interactive computer programs to educate on Mashantucket Pequot life through the ages.
But the coolest exhibits are the life-size dioramas.
Visitors start their visit in a simulation of a glacial crevasse in the last Ice Age. There, they can watch a simulated hunt by the ancestors of the Mashantucket Pequots, complete with the sound of creaking ice and winds.
Follow the path into a completely recreated 16th century coastal Pequot village to get a life-size view of life before the arrival of Europeans.
The learning experience continues with more exhibits about life from 1675 until the 1970s.
But nothing else compares to those expansive dioramas, in this writer’s opinion.
Connecticut was the home of America’s nuclear submarine production.
And this Cold War holdover still has a presence in Groton, Connecticut at the Submarine Force Museum.
Head to the only museum in existence managed by the United States Navy to explore the world’s first nuclear-powered submarine.
Other items in the museum’s collection highlight the history of submarines from inventor David Bushnell, a Connecticut native, and his Turtle, constructed in 1776.
While Mystic, Connecticut, is itself an attraction, one of the lesser-known things to do in the area is certainly one of the most unique points of interest in the entire state.
Possibly the country.
Sitting off the coast of Connecticut, accessible by a causeway, sits Enders Island.
Originally a private estate, the Society of St Edmund, a group of monks, now own and occupy it.
This order started in France, but fled to the United Kingdom in the 19th century before settling on Enders Island, always traveling with their religious relic.
Today, that macabre relic is viewable in the chapel on the island: the severed arm of St Edmund.
Make the trek to see this Gothic holdover, and recreate your own medieval pilgrimage.
The island is lovely, too, and worthy of its own pilgrimage for an afternoon.
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Connecticut offers a culinary tour of historic and futuristic firsts.
The battle line of lobster roll devotees fluctuates, but there are two schools of thought for what a real lobster roll is: Maine and Connecticut.
And it’s largely a difference between mayonnaise and butter.
A Maine lobster roll is lobster meat tossed with mayonnaise in a buttered and toasted hot dog roll, served cold.
The Connecticut lobster roll, meanwhile, is hot lobster meat dressed with butter and served in a warm, toasted bun.
Doesn’t that sound way more delicious?!
The Connecticut lobster roll first appeared in the 1920s at a now-closed restaurant named Perry’s in Milford, Connecticut.
You can’t enjoy a Connecticut lobster roll in its birthplace, but it was such a hit here that this dish spread up and down the Connecticut coast.
Head to the Lobster Bin in downtown Greenwich for what is arguably the best lobster roll in Connecticut.
Some other Connecticut restaurants serving great lobster rolls include:
Save an appetite for the home of a heavy-hitting first in America, in New Haven, Connecticut.
Many places claim to be the birthplace of the hamburger.
But the Library of Congress declared Louis’ Lunch in New Haven, Connecticut, the official cradle of this most American dish.
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That said, they’re a bit stern in their requirements of enjoying a hamburger their way. Their stipulations include:
Louis’ Lunch was originally a lunch truck owned by the eponymous Louis Lassen. In 1900, a customer ran up and asked for a quick lunch to take with them.
Mr Lassen took trimmings from his more typical steak sandwiches, put it between two pieces of toast, and sold it to his customer.
Today, Louis’ Lunch has occupied the same location since the 1970s. They’re open for lunch and dinner, Tuesday through Saturday.
New Haven is home to a fantastic dining scene, beyond being the birthplace of the hamburger.
Pizza restaurants here frequently win national awards.
But one of the most interesting and unique restaurants in New Haven is the home of “future sushi”.
At least according to the current owner, Bun Lai Yoshiko.
Bun Lai’s mother, Japanese immigrant Yoshiko Lai, opened Miya’s Sushi in 1982. It holds the title for being the world’s first sustainable sushi restaurant.
Decades later, it remains a local favorite earning national recognition.
And Bun Lai has created an innovative menu serving local invasive species.
The Future Sushi Voyage tasting menu offers an experience in Bun Lai’s vision of what the sushi experience may offer in 2150. While not your typical fare, be ready to try sashimi featuring such threats to native flora and fauna as:
That last one is native. But the white-tailed deer population has exploded in Connecticut without predatory species to keep them in check, wreaking havoc on native plant populations.
Many of these unique ingredients are often foraged by Bun Lai himself.
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The menu may even include an insect or two, if you’re feeling particularly adventurous.
Be sure to wash it all down with such house-made infused sakes as watermelon chili.
If you’re looking for something truly unique to Connecticut, look no further than the seasonal restaurant, the Place.
Open May through October in Guilford, this entirely open-air camp kitchen cooks all its dishes over a fire pit since it opened in 1971.
The menu has simple and delicious local staples. Steak and chicken are options for the more squeamish, but the draws are the seafood:
The clams alone are a huge draw. The cooks put littleneck clams in the fire until they open, then douse them in a mixture of cocktail sauce and butter.
And everything is served on their firetruck red tables with tree stump seats.
Dining here is definitely a unique experience.
While the classic American fare at the Griswold Inn is worth a visit, the most intriguing part about the Griswold Inn is its history.
The Griswold Inn is the among the oldest of America’s continuously-run taverns. This despite such historic hurdles as invading British troops (Essex is one of the only towns in America invaded by a foreign power) and Prohibition.
This pizza place is most famous for the movie named after it.
Open since 1973 on the main drag of Mystic, Connecticut, all pizzas are made with a “secret sauce”, the recipe of which, just like in the movie, is a mystery to outsiders.
And just like in the movie starring Julie Roberts, the restaurant is strikingly similar to the one in the movie, though it wasn’t shot on location.
TV screens inside Mystic Pizza run the movie on a continuous loop, in case you need a refresher.
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During the Revolutionary War, Connecticut was known as the arsenal of America, as it was the most industrialized state in the Union.
New Britain was later the source for not only many manufactured goods in the 1800s, but also the machines and know-how to operate them.
And peddlers traveling the American frontier were stereotypically from Connecticut.
So of course Connecticut has some unique places for retail therapy.
What was once a muddy country road in a backwoods town is now one of the most cosmopolitan shopping districts in America.
The downtown Greenwich Avenue shopping district is a destination for all of Connecticut and beyond for the huge number of high-end luxury boutiques that line the street. It has still maintained its local offerings, as well, to keep what you’ll find here unique and interesting.
The City That Works, next door to Greenwich, hosts an entire antiques district for aficionados.
These are no flea market finds, however, you’ll find some of the best preserved antiques from any period for which you’re searching.
And you’ll pay top dollar for them.
Some of the top Stamford antique shops include:
With one of the earliest public school systems in the country, Connecticut has long had a high literacy rate.
So our small population has a high proportion of avid readers, and unique shops to serve them throughout Connecticut.
This cozy little shop is just off of Greenwich Avenue on Grigg Street in Greenwich.
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Books are carefully and lovingly curated, with little descriptions and teasers hand-written above each book on sale.
Diane’s Books is worth perusing whenever you’re shopping Greenwich Avenue.
A New Haven institution since 1976, the Atticus Bookstore on Chapel Street is a prime spot to rub shoulders with Yale students while grabbing a coffee and searching for an unexpected literary find.
This bookstore on the main street of Madison, opened over two decades ago with a mission to be a place where writers meet readers. R. J. Julia Booksellers hosts over 200 events a year, hosting authors from around the country.
What began as a singular structure devoted to books has expanded to about half a million literary works, sprawled across five different buildings and even makeshift structures.
Book Barn in Niantic, Connecticut, requires some exploring, based on your personal literary interests:
You’re guaranteed to get lost in here for hours, and you can even take breaks at the playground on-site.
Another Mystic contribution to the list of unique things to do in Connecticut, Olde Mistick Village is more than just a tourist trap.
Just off of I-95, Olde Mistick Village is modeled after a New England colonial village, complete with such touches as:
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The brick pathways connect the more than 40 shops sprinkled throughout the area, selling gifts from around the world.
And the quaintness gets kicked up a notch around Christmas time, when the Christmas shop on-site likely makes the vast majority of its sales.
That said, Olde Mistick Village hosts musicians, dancers, storytellers, and more events in the gazebo and meetinghouse throughout the year.
Sure, everywhere has a pumpkin festival, an arts and crafts festival, and the like; but where else on this continent can you burn an effigy of a public figure?!
That isn’t Burning Man, anyway.
Explore Connecticut for some of the best events distinctive to our corner of New England.
The cute, affluent Norwalk neighborhood of Rowayton hosts an annual tradition that locals love.
Shakespeare on the Sound hosts 16 performances in the open-air of Pinkney Park in Rowayton for two weeks each summer.
While the goal of the production is to make Shakespeare accessible, that doesn’t mean they skimp on quality. In fact, the performers hail from:
Sound expensive? There’s a suggested donation ticket price, though it’s not required.
Bring a blanket and a picnic to stake your space and make an evening of it. It could very well be one of the most romantic things to do in the summertime in Connecticut.
But bring bug spray, just in case.
Each September, Westport, one of the most charming towns in Connecticut, hosts a culinary event celebrating one of the most well-known New England fares: clam chowder.
Chowdafest happens annually in Sherwood Park. Guests can sample and judge more than 40 different chowder recipes from various restaurants.
Categories judged include Classic New England Clam Chowder and Most Creative Chowders.
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Centuries later, New London, Connecticut, still really dislikes Benedict Arnold.
It’s hard to blame the city: Benedict Arnold was from nearby Norwich. But his story went sour after he turned traitor and fought for the British in the Revolutionary War. He slaughtered surrendering forces after capturing New London, then burned the city to the ground.
In fact, Arnold specifically ordered that “every building should be on fire.”
The people of New London never forgave him. To this day, locals hold such a grudge that Benedict Arnold’s name is used as a severe insult synonymous with traitor.
Locals also use it to imply an intended arson.
And starting just a year after the burning in 1782, the citizens of New London carried a two-faced effigy of Benedict Arnold before burning him. The tradition of parading and burning the traitor’s effigy continued until the Civil War, and restarted in the last decade.
The curious, or those who sincerely hate Benedict Arnold as well, can head to New London in September to witness the parade and burning. Check for the exact date each year before you go.
All of the best free attractions, activities, and things to do across the state; from the Submarine Force Museum to Steep Rock Preserve.
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Thanks to its reputation, many assume stereotypically wealthy Connecticut is lacking in the cheap and free things to do department.
But that’s far from the truth, regardless of where in the state you are.
Much of this list of free things to do in CT I discovered during the Covid pandemic.
During the pandemic lockdown in the spring of 2020, almost anything free and outdoors was fair game.
Major exceptions were state parks, though hiking in state forests were still open to the few who know of them.
Even after the lockdown was lifted in Connecticut, money remained tight. As such, free stuff remained the way to go, either indoors or outdoors.
So, ready for a whirlwind tour of Connecticut for cheapskates, from its shoreline up to the mountains of Litchfield?
Read on for our list of top free things to do in Connecticut.
The term “southern Connecticut” is a tad confusing.
How does one decide what is “southern” in a rectangular state, smaller than 6,000 square acres?
Whatever you want it to be.
I decided that any towns touching the Connecticut shoreline is Southern Connecticut for the sake of this article.
And to quote RuPaul, “My show, my rules.”
With more than 332 miles of shore, Connecticut’s coastline offers plenty of opportunities to explore.
Starting from our hometown of Greenwich, and heading eastward all the way to Stonington on the border of Rhode Island:
What journalists call the hedge fund capital of America is known for the wealth of its citizens.
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But that doesn’t mean you can’t plan an entire weekend getaway here without spending much money.
Especially if you’re into window shopping, long walks on the beach, and hiking in the woods, it can be a paradise without blowing too much cash.
Downtown Greenwich was once a small, provincial borough that has grown into a cosmopolitan shopping destination to rival others throughout the country.
Many visitors compare the Greenwich Avenue shopping district to Rodeo Drive in Beverly Hills, California. I think another comparable shopping main street would be King Street of Charleston, South Carolina.
Many shoppers come to spend fortunes at the elegant clothing boutiques, jewelry stores, and other luxury brands. That doesn’t mean you’re obligated to do so, window shopping is always free on our beautiful main street.
Free or no, window-shopping and people watching on Greenwich Avenue is one of the most unique things to do in southern Connecticut.
Jutting out into Long Island Sound from the Old Greenwich neighborhood is Greenwich Point Park. Locals know it better as Tod’s Point, after the wealthy industrialist who first filled-in a swampy cluster of islands to create the peninsula.
Greenwich Point Park is definitely the best of the beaches in Greenwich, and one of the most beautiful on the Connecticut coast.
That said, it’s not free to visit year-round.
During the height of the summer season, only Greenwich residents and non-residents willing to pay for hefty beach passes get to step foot on the park.
Come winter, though, it becomes one of the best free things to do in Connecticut in the winter.
It makes the list because a walk along the trails of Greenwich Point Park is a splendid winter activity.
Be sure to walk to the southwestern-most edge of the park to see a sweeping view of the distant New York City skyline on a clear day.
After living elsewhere for much of my twenties, I came to appreciate Connecticut for the fact that you can go from the beach to uphill hiking within an hour.
Not many other states can claim that!
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And there are a ton of hiking trails near Greenwich, Connecticut. A few personal free favorites include:
There are a couple options as far as free things to do in Stamford, the city next door to Greenwich. Aside from walking around the downtown, a few other free activities in Stamford include:
This park with varied terrain in a manageable space, is only a little over 90 acres. Going for a hike at Bartlett Arboretum is especially pretty in the fall, but any season is lovely.
While nowhere near as famous as the Maritime Center or Mystic Aquarium, this place is impressive as far as free attractions go.
Situated in Cove Island Park, close to the Sound it is focused on studying, Soundwaters Coastal Education Center is home to hundreds of species native to the surrounding coastal habitats.
Afterwards, wander through the larger ecosystems throughout Cove Island Park.
Be warned that parking can be a pain at Cove Island, especially in the summer months.
Drive up the Connecticut coast from Greenwich and Stamford to reach Westport and its inland neighbor, Wilton.
Walking through the two downtowns of these top picks for cute towns in Connecticut is a great free activity, but there are other free attractions here, as well.
The history of this observatory is just as interesting as the night sky.
The Observatory at the Westport Astronomical Society is housed in a former Nike radar site. The Federal government built these sites around major cities throughout the United States during the Cold War. The purpose of this site, in common with others, was to both detect a Soviet strike earlier and provide anti-aircraft defense protection.
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The US Army demolished the missile silo before selling the property to the town of Westport, but many of the former base’s buildings remain.
One of which is the former radar pedestal that the Astronomical Society uses as support for their 12.5-inch Newtonian telescope.
They also regularly host a 25-inch Obsession telescope on the lawn, which they bill as “the largest in Connecticut available to the public.”
The Society opens their observatory to casual observers every Wednesday for free from 8 to 10pm for viewing the skies.
Even if you’re not a huge astronomy nerd, star gazing is one of the most (free) romantic things to do in Connecticut at night.
Head inland from Westport, or along Route 7 and the Norwalk River from Norwalk to get to Wilton.
This cute little town is most famous for the Weir Farm National Historic Site.
This was the summer home of Impressionist painter Julian Alden Weir. Today, this 60-acre site is the only national park dedicated to painting, as an important site for the American Impressionist art movement.
The landscape here has inspired painters for over a century, and you’re welcome to explore the grounds for free to understand why.
While much of the former open fields have since filled-in with trees, it’s still a beautiful place to hike after taking the brief 30-minute tour of the house. And depending on when you’re visiting, bring a picnic to enjoy on one of the well-maintained lawns.
There are even free art supplies for those who are so inspired by the surrounding scenery.
At about the middle point of the Connecticut coast between Greenwich and Stonington sits New Haven.
This city is most famous for the very prestigious university that occupies a large portion of its downtown: Yale University.
And the university hosts a large number of the best free things to do in New Haven.
In fact, the list of free activities here is a bit long.
How to manage it all?
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With a walking tour!
Walking from the first point on the list, close to New Haven’s Union Station and where I-91 meets I-95, you could walk to or through every attraction on this list in about an hour and 20 minutes.
But you wouldn’t be able to stop anywhere, and you’d be pretty tired by the end after walking up a massive hill.
But walking is the most free way to get around, so up to you.
Compared to the museums of Yale University, visitors often overlook the Knights of Columbus Museum.
But this architecturally striking modern structure hosts both the museum and the headquarters of America’s largest Catholic fraternal organization. As befits the theme, much of the exhibition space is devoted to the history of Roman Catholicism in America.
A display of creches and nativity scenes from around the world is an annual holiday tradition here.
And with free parking as well as free admission, why not pass a few pleasant hours here?
Walk into downtown New Haven for about 10 minutes to reach New Haven’s City Green.
In the middle of the Green sits the Center Church.
This United Church of Christ religious site was built in 1813. Church members often offer free tours to show some of the more interesting parts of the building, including:
But the most interesting point of this church is what’s underneath.
The congregation built this church over New Haven’s oldest burial ground. Rather than move the remains or gravestones, the church’s crypt was built to hold and protect the area.
And this crypt is now one of the best preserved in New England. Dates on the gravestones stretch from 1687 to 1812 and feature names of the area’s founders and earliest citizens. Some notable names include:
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While the jury’s still out on whether this is one of the most haunted places in CT, it’s one of the most interesting.
Walk for about 6 minutes along Chapel Street to hit the next free New Haven attraction.
The Yale University Art Gallery is the oldest college art museum in America. It has grown from its founding to become a world-class art museum that easily competes with collections in New York City and Boston.
The Gallery holds 250,000 objets d’art that span human history and across the globe. The museum is especially notable for its ancient Greek and Roman artifacts, African art, and early Italian Renaissance paintings. That said, its collection of contemporary and modern art includes such heavy hitters as Miró, Basquiat, Picasso, Degas, and Rothko.
Even the architecture is a marvel. The Yale University Art Gallery stretches across a block and a half in three buildings, each of a distinctly different architectural style. Visitors enter the modern marvel designed by Louis Kahn in 1953.
And it’s seriously free!
If you haven’t, somehow, developed museum fatigue from the last free attraction, walk across the street to the Yale Center for British Art.
The Yale archives basically realized that the Yale University Art Gallery was too much in one building, so they took the largest single collection and put it across Chapel Street.
And this collection is massive. The Yale Center for British Art holds the largest collection of British art anywhere outside of the United Kingdom.
While one former guest complained that this museum was just “a never-ending parade of ship paintings”, there is more than that here.
Three hours could get you through almost all of this collection of many of the greatest British artists of the 18th and 19th centuries.
There are plenty of landscapes, portraits, and paintings of ships.
And this New Haven, Connecticut museum is also free, though neither this, nor the Yale University Art Gallery, is open on Mondays.
While walking between all the amazing free museums hosted by Yale University, be sure to admire the campus itself.
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The Old Campus Courtyard hosts one of the oldest academic buildings in continuous use in America.
And the entire campus of one of the oldest and most prestigious universities in America was designed to match the historic grandeur of the even older universities of Cambridge and Oxford.
In fact, the builders poured acid down the stone walls of the buildings after they finished construction to make them look older. The acid quickly degraded the mortar holding the stones in place, and within a short span of time, the buildings started to shed stones onto the sidewalks below.
The second time around, the builders left nature alone to do the weathering for them.
Yalies were almost called Dummies, but were saved by a large donation from a wealthy local merchant of the name Yale.
How do I know all this? By taking the campus tour, full of Yale history and campus myths. Yale University offers them for free.
When there isn’t a pandemic going on, anyway.
The campus, with its varied architecture and mature trees, is beautiful at night and during the day. The carillon bell ringing at 6 and 7 pm is beautiful and adds to the European charm of the experience.
This building is a true marvel, built in 1962.
It is the largest building in the world dedicated to the collection and preservation of rare manuscripts and books.
And while the collection is awe-inspiring, it is the building itself that leads visitors to describe this as a magical place. To help preserve the collection, the building is covered with translucent marble to keep harsh light from damaging the materials. And when those marble windows are lit well enough to illuminate the interior, the sight is spectacular to behold.
The oldest printed item in the collection is a Gutenberg Bible. It’s one of only 48 known surviving examples, printed approximately in 1454. John James Audubon’s Birds of America collection is also a major draw. Both are on display in the mezzanine of the Beinecke Rare Book & Manuscript Library.
The most curious item in the collection, however, is not. The mysterious Voynich Manuscript, also known by its call number, Beinecke MS 408, continues to intrigue visitors.
This manuscript is named for the book dealer who purchased it in 1912, but its origins are a mystery.
The book was donated to Yale’s collection in 1969. And to this day, scholars and code-breakers continue to attempt to understand the riddles and mysteries of the manuscript. The manuscript is written entirely in a strange and likely fictional language and elaborately decorated with symbols and illustrations of fanciful plant life.
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While the Voynich Manuscript is not on display, a facsimile is by the front desk.
You too can play Indiana Jones when you visit this library, for free.
A 15-minute walk will bring you to the Yale Peabody Museum of Natural History.
The exterior of this natural history museum looks like a cathedral, which contributes to an understanding of why this institution is called “the Sistine Chapel of Evolution.”
The Yale Peabody Museum of Natural History recently celebrated its 150th anniversary. The museum largely started as a gem collection, but has since expanded into one of the most influential museums and research organizations in the world.
The most famous room in the museum, and my personal favorite as a kid, is The Great Hall of Dinosaurs. This awe-inspiring room features a mounted skeleton of a young 110-foot Brontosaurus. It also contains reconstructed skeletons of:
And on the wall is the famous mural The Age of Reptiles by Rudolph Zallinger.
In fact, the Peabody Museum has one of the largest and historically important fossil collections in America, partly thanks to Othniel Charles Marsh’s part in the Bone Wars.
Other major collections include:
The museum also has permanent exhibitions dedicated to mammal and human evolution, Egyptian artifacts, wildlife dioramas, and Native Americans of Connecticut.
But there’s a catch.
The Yale Peabody Museum is only free to visitors between 2 and 5 pm on Thursday afternoons from September through June.
And it’s currently closed for a major renovation as of 2020.
But once it reopens, it will be worth the visit. Its collection has even come full-circle, with a new multimillion-dollar gem hall.
Walk 40 minutes, mostly uphill, to get to the final destination on this walking tour, East Rock Park.
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A bike ride up could be strenuous, but pretty.
Or just drive.
But however you get here, you’ll enjoy the view at the top once you are there.
All of New Haven to the harbor and Long Island Sound stretches out below East Rock Park.
And sitting here to watch the sunset as birds cavort in the gathering gloom of dusk puts East Rock Park high on the list of free romantic things to do in CT for couples.
The park also features hiking trails, and one of the most impressive military monuments in the country in the Soldiers and Sailors Memorial.
Of course the city hosting some of the most prestigious institutions in America would host free Shakespeare performances.
And so the Elm City does.
The Elm Shakespeare Company hosts Shakespeare in the Park every summer at Edgerton Park in New Haven.
Bring a blanket and a picnic so you can stake a claim on the lawn early with a great view of the stage and enjoy the magic of Shakespeare, all for free.
The largest arts and culture festival in Connecticut is an annual fixture in New Haven.
For a few weeks in June, some of the brightest artists, writers, and thinkers of the world descend on the city. While many programs of the International Festival of Arts & Ideas charge admission fees, many more are free to the public, including the free concerts on the New Haven Green.
Once you’ve finished enjoying the overwhelming amount of free things to do in New Haven, there’s still more to explore in surrounding towns.
In a state where waterfront mansions sell for millions of dollars, and towns battle in court to keep their beach access limited, it’s amazing there are still free beaches.
But Silver Sands State Park is free to the public, for now.
A nice boardwalk hugs the beach from here to Walnut Beach, another neighborhood in Milford.
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And the beach is a gorgeous place to watch the sunrise or sunset, regardless of the time of year.
Charles Island sits just off the coast of Silver Sands. Legend has it that Captain Kidd left a buried treasure behind, though no one has ever found it.
If you’re feeling lucky, you can walk out to the island at low-tide to search for treasure. Be sure to allow yourself plenty of time to get back before the bridge gets covered by water again. Also, stay away from the interior of the island in the summer, when it’s home to heron and egret breeding rookeries.
The state has a planned $10 million project to add a concession stand, bathrooms, improve parking, and implement a parking fee. Many residents oppose it, but you may need to hurry to enjoy the park while it’s still free.
Osborndale is a 417-acre park sprawling along the east bank of the Housatonic River.
The park is named after Osborndale, a Colonial Revival House on the National Register of Historic Places. American industrialist, philanthropist, and dairy farmer Frances Osborne Kellogg lived and raised award-winning Holstein cattle here.
Before her Holstein and Jersey cow farming operations, the site was mined for silver in the post-Revolutionary War period, and used as a site to bottle spring water.
After Ms Kellogg willed the property to the people of Connecticut in 1956, it has become a recreation site. Visitors can come to Osbornedale State Park for free to enjoy:
This park just north of New Haven is a great weekend hiking trip, especially during the Connecticut fall foliage season.
The trails can get busy and parking is limited, but you can park on the street.
The easy trail is about a 45-minute walk, one way, over a trail that includes stretches of gravel and rocks.
Once you get to the top, you can check out the view from the observation tower, have a snack, and snap a couple pictures.
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Castle Craig is one of the more intriguing towers in a state full of towers built on hills.
I didn’t realize how many are in Connecticut until exploring the state during the Covid pandemic.
Castle Craig, perched on a cliff overlooking Meriden, looks like it’s all that’s left of the ruins of some long forgotten fortress.
In reality, it and the park surrounding it was a wealthy man’s gift to the city below.
Walter Hubbard, a wealthy industrialist, commissioned the tower with a design inspired by his extensive travels. Visitors see a medieval Turkish tower, others see French Norman influence. It looked more like an ancient Scottish ruin to me, but the design is a mystery to everyone.
Not only did Mr. Hubbard build this tower on a hill, he also hired the Olmsted Brothers, the sons of the man who designed Central Park in Manhattan, to lay out the design of the park below.
Once the work was completed, Walter Hubbard donated the entire property, tower and all, to the city of Meriden in the early 20th century.
The base of the hill features a manicured park where locals come to get their photos. Further in, the terrain gets wilder and includes a large pond and dense forest.
There are several hiking trails of varying difficulty, the white-marked one leads up to Castle Craig. The final few hundred feet ascent are a steep scramble over rocks, but it’s well worth the view.
You can also walk on the road that loops around the pond and up the hill. That road is open to cars in the summer months, but you have it to yourself once they close it to vehicles after October ends. The walk takes longer, but it’s more relaxed and a much gentler slope.
A few words of warning for this free attraction in Meriden:
There are no restrooms or water fountains at the top of the hill, so plan accordingly.
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In addition, there are very few barriers separating you and a straight drop down the side of a cliff at the top. So use your common sense and don’t become the reason that the city of Meriden feels obligated to erect barriers partially blocking the view for everyone that visits after you.
Head due East from New Haven to reach Connecticut’s most popular tourist destination: Mystic, Connecticut.
Thousands of people can visit this quaint little town on any given day in the summer. Many of its most popular attractions are not cheap: Mystic Seaport and Mystic Aquarium being top activities.
But all is not lost! There are plenty of free things to do in Mystic.
Dividing one stretch of Mystic’s cute downtown from the other is the Mystic River, the namesake of the town.
And providing passage across is the Bascule Bridge of Mystic River.
A bascule bridge is a fancy word for a drawbridge. It’s a moveable bridge that uses a counterweight to balance a span with an upward swing so that boat traffic can pass underneath.
The most famous bascule bridge is the Tower Bridge in London. The second most famous one is in Mystic.
Maybe.
It’s still cool to watch it operating. Sit by the side of the Mystic River, ideally with ice cream from Mystic Drawbridge Ice Cream or pizza from Mystic Pizza, and watch the bridge in action.
Summer months are ideal, when the amount of boat traffic passing through keeps the bridge moving at least once an hour.
Speaking of which, walking around downtown Mystic is another delightful, and free, experience.
If you’ve already dropped a lot of money at Mystic Seaport, you can easily follow the river down to Long Island Sound.
In the warm months, Mystic is a charming and busy little town straddling the mouth of the river. It’s full of shops and restaurants, and even a few historic inns.
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Even if you’re not interested in spending money, a stroll among the calm pedestrian traffic is pleasant for admiring the historic architecture lining Main Street. And the beautiful historic homes along the residential streets, especially the Stonington side of town, warrant at least a few photos, especially with the glistening water behind them on a clear day.
A 42-minute walk (or 6-minute drive) from downtown Mystic is a New England style tourist trap.
Not casting aspersions, it is quite charming.
Olde Mistick Village is an outdoor mall constructed to look like an 18th-century village. The complex of 60 small shops and many eateries are right next to Mystic Aquarium.
Walking around and looking in the various shops is another pleasant and free way to spend an afternoon.
Small boutiques scattered around the village offer such visual delights as accoutrements from Ireland or the Himalayas, Christmas decorations, and even handmade jewelry.
My strongest memory from any childhood trip anywhere in New England was the fudge at some old-timey General Store.
And Franklin’s General Store offers that, plus the many unexpected items you’ll find in a typical general store.
Don’t forget that looking and smelling is free.
A 10-minute drive from downtown Mystic will bring you somewhere that feels a world away.
Enders Island is one of those hidden, unique, treasures of Connecticut.
Like many public and semi-public spaces in Connecticut, Enders Island was a private estate with an Arts and Crafts style mansion at the center.
The final private owner willed the island to the Catholic Society of St Edmund, who continue to occupy the space and host a retreat center and art school.
The outdoor spaces are open to the public for quiet reflection. The garden paths throughout the property are still marked with the imported Italian tiles from when the Enders owned the island.
And displayed in the chapel is a throwback from the Middle Ages.
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The Society of the Fathers and Brothers of Saint Edmund have been responsible for the relics of their namesake since the 19th century. The Edmundites were evicted from France in 1903 due to “government anti-clericalism”. They first relocated to England, then settled in Mystic, all the while carrying the severed arm of Saint Edmund.
The shriveled, blackened arm of Saint Edmund resides in an oblong glass container in the Chapel of Our Lady of Assumption on the island.
Once you’ve explored Mystic, there are even more free attractions in the surrounding Connecticut beach towns.
Head east from Mystic towards the Rhode Island border to find the historic town of Stonington.
The downtown of this old whaling town is charming and well worth wandering through for the day. The homes are clustered close together, with barely space between them for small alley gardens, in some cases.
A writer described this town as a piece of Nantucket, swept to shore. And between its cute shops, gorgeous views of the harbor, and quaint touches like having Connecticut’s last fishing fleet docking here, it’s easy to understand the reference.
During the Cold War, Connecticut was the center of nuclear submarine construction.
The first nuclear-powered submarine, the USS Nautilus, was completed in Groton in the 1950s. And it instantly became the fastest and most powerful underwater vessel in the world up to that point.
Over its 25-year career, the Nautilus traveled half a million miles on missions across the world, including up to the North Pole. It was parked by the Submarine Force Library & Museum after its decommissioning in 1986.
Visitors to the museum, the only one operated by the US Navy, can get below deck of the Nautilus and learn about the operations of staying underwater for months without coming to the surface.
You’ll also get a feel for the tight quarters these sailors tolerated for months on end.
While the Nautilus is the centerpiece of the museum, there is also a fantastic collection of artifacts tracing the history of submarines from the Turtle, designed by Connecticut inventor David Bushnell and used during the Revolutionary War, to the present day.
This 800-acre park near the Groton-New London airport is ideal for hiking or walking.
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The main loop trail includes plenty of turn-offs to admire the ocean views, or sit and have a picnic lunch. The main beach is not a major draw, as it’s mostly rocks and seashells. But that means that this free attraction is not often busy.
To the north of the city of New London sits one of the largest arboretums in Connecticut.
The Connecticut College Arboretum started as a 64-acre tract of mature hemlock trees in 1934, and has since expanded to 750 acres of diverse landscape. All to help visitors better understand the botanical world.
The Caroline Black Garden is a five-acre garden of native and exotic ornamental woody plants first established in the 1920s. The Native Plant Collection is 30-acres of plants indigenous to Eastern North America, while 120 acres of woods and shrubs from around the world make up the Campus Landscape.
Keep your eyes open for views of the Thames River and Long Island Sound.
And be sure to bring strong bug spray in the summer months, just in case.
Next, drive south from the Arboretum through New London towards Goshen Point.
Harkness Memorial State Park sits on the furthest south tip of the broad peninsula jutting down from New London.
Eolia, the mansion on-site built by the Harkness family in 1906 as a summer home, is ornate and lovely. But the almost panoramic views of the Sound from the house are even more impressive. And the surrounding gardens, lawns, and grounds are worth exploring.
In fact, much of the park offers gorgeous views of the Sound, especially on a sunny, bright day.
There are plenty of photo opportunities for the aspiring, or professional, photographer throughout the gardens.
But there’s a catch.
While parking is free for Connecticut residents, the charge is $15 for out-of-state license plates. But if you bring a picnic or barbecue and spend the day, it’s well worth it.
Essex is one of the few American towns to ever be attacked and burned to the ground by enemy forces.
But Essex rebuilt after the War of 1812, and built back better to create the adorable town it is today.
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Walking around Essex, visiting the cute shops, and admiring historically significant spots like one of the oldest continuously-operated taverns in America, is all free to do.
And a delight anytime of year.
Be sure to check out one of the towns that inspired the fictional town Stars Hollow from Gilmore Girls.
John Oliver may not be a huge fan of Danbury, but he will allow that one of the free things to do on this list is worth a visit.
Perhaps we’ll someday add The John Oliver Memorial Sewer Plant in Danbury to this list of free things to do in Connecticut.
Though I doubt it.
Locals more often associate this idyllic park and its restored mansion with picture-perfect weddings and other events.
But a lake, two ponds, multiple picnic areas, and 21 miles of hiking trails also await at this 722-acre municipal park.
But in a state full of castles and castle-like towers, Hearthstone Castle is the most romantic.
New York photographer E. Starr Sanford first treated Tarrywile Park as his summer retreat.
He built the castle between 1896 and 1899 to have 16 rooms, including:
While the exterior was made from local stone, the wood was largely imported from Italy. Some of the wood still survives on the building’s veranda.
After Danbury acquired the estate as a municipal park, the once grand Hearthstone Castle declined gracefully. The ruins of the castle are now ensconced in the woods, as if from a fairy tale.
As of 2016, the city of Danbury decided to maintain the castle as a walled garden. Hopefully this free Danbury attraction will remain in its current romantic state for many more generations.
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The Flanders Nature Center, an over 2,000 acre preserve, started about 50 years ago to preserve a vestige of the agrarian nature of Woodbury.
The trust started when Natalie Van Vleck, accomplished artist and turkey and sheep farmer, donated the farm to the trust on her death.
The hiking throughout is splendid, with four miles of trails through an orchard, meadows, marsh, pine forests, streams, and more. And educational opportunities abound throughout the property, including learning about the industry of making Connecticut maple syrup at the sugar house on-site.
In the middle of the achingly quaint New England town of Newtown sits an abandoned psychiatric hospital.
A system of deep tunnels plies the ground under the hospital’s former campus. They lead to confinement rooms, operating rooms, psychosurgery laboratories, and a morgue.
This former institution that once housed over 4,000 patients made the list for being one of the few haunted places in Connecticut that don’t require visitors to do anything illegal to visit for free.
Within limits, of course.
The tunnels and unused buildings are inaccessible to the public (and trespassing is illegal), but much of the campus is open for public use. Meander through the roads, sidewalks, and trails along with local joggers and dog walkers to explore this spooky site used in the 1996 movie, Sleepers, as the Wilkinson School for Boys.
Want to experience the great outdoors and wide open spaces the way Connecticutians do?
Then hoof it to Litchfield County, with more deer than people.
The vast expanses up here mean there’s lots of free hiking and exploring to do in the Berkshires of Connecticut.
Litchfield is one of the most cute towns in Connecticut.
Wandering along its well-preserved downtown is a delightful, free, thing to do here.
But while you’re here, take a short walk away from West Street to one of many firsts in Connecticut, and a top free historic attraction.
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Tapping Reeve and his wife, Sally Burr Reeve (sister of Aaron Burr of Hamiltonian fame) settled in Litchfield in 1773. Mr. Reeve established a legal practice, to which Aaron Burr came to live with them and learn the legal profession.
As more wealthy locals sent their sons to Reeve’s practice for legal training, his law profession expanded into America’s first formal law school. By the time the Tapping Reeve House & Law School closed in 1833, more than 1,100 students had matriculated.
Visitors today can experience the life of a Revolutionary era law student with role-playing, interactive and hands-on exhibits.
Have you heard one too many lawyer jokes in your life to want to see how the first American ones were developed?
Then you can do what the locals do and strap on your hiking boots.
Just outside of town sits 4,000 acres of preserved forests, wetlands, and fields along Bantam Lake.
The White Memorial Conservation Center’s 40 miles of trails could take days to fully explore, and all for free.
Outdoor enthusiasts love to hike, bike, and ride horses on the trails in warmer months. The ponds, Bantam Lake, and six miles of the Bantam River are fantastic for canoeing, kayaking, and fishing. And the trails here are the best in the state for Connecticut winter activities like cross-country ski, and snowshoeing.
The Little Pond Boardwalk Trail is especially popular, with a wooden boardwalk traversing above the edges of the pond’s woods and marshes.
Washington Depot is another town that inspired Stars Hollow of Gilmore Girls.
But Steep Rock Preserve provides experiences reminiscent of many epic adventure movies coming out of Hollywood.
Visitors can:
And accessing all of this 974-acre preserve is free.
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Like Bridgeport on the Connecticut shoreline, Hartford is a fascinating place for visitors intrigued by places which have passed their glory days.
Hartford was once a major cultural and financial center, hosting such famous inventors, industrialists, and artists as Samuel Colt and Mark Twain.
It’s a classic example of killing the goose that laid the golden egg.
Hartford tore down much of what would later be considered charming about the city in the interest of following trends considered modern.
In this case, Hartford was busy making sure that the automobile was king, with:
These changes made in the Post-War era have had lasting effects on various parts of Hartford’s attempts to bounce back from its Rust Belt image, including hits to the city’s tax base and liveability.
All that to say that Hartford is still a great place to visit. Hold-overs from its heyday, like museums and state government sites, match the more modern renaissance of its artistic and gastronomic scenes.
Many of those historic hold-overs are great free things to do in Hartford, CT.
Look to your left while driving up Interstate 91 from New Haven into downtown Hartford and you’ll see something that appears to be out of place.
A giant onion dome, swathed in bright blue and adorned with gold stars, sits atop an old industrial building right by the highway.
Many visitors to Hartford comment that this building has more in common with Eastern Europe than Hartford, and think nothing more of it.
But this building is actually part of a national historic park, honoring the industrialist who founded it, and the artisans who worked for the family’s company.
Most Americans have heard of Gerald Ford, but not as many non-gun owners have heard of Samuel Colt.
Mr Colt patented a mechanism that allowed a revolver to fire multiple times without reloading.
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Western cowboys would not have had their most famous tool on them in the movies were it not for Samuel Colt’s innovation.
And this revolver was manufactured for decades in the east armory of the factory supporting that blue dome.
In fact, the entire campus of Coltsville became a model of 19th century industrial paternalism, something Gerald Ford took to further extremes in the early 20th century.
At its heyday, Coltsville included everything its workers needed to enjoy a quality life:
Today, the National Park Service is setting-up more consistent opportunities to explore Coltsville National Historical Park, including such architectural masterpieces as:
Both Elizabeth Colt commissioned as memorials to her husband and son, respectively.
After exploring Hartford’s symbol of 19th century industrialization, head into downtown Hartford.
Follow signs for the State Capitol to reach Bushnell Park, an oasis in the heart of the city.
In a state of many firsts, this was the first public park in America financed with public funds.
And the park remains a haven to this day, with a restored 1914 carousel, memorials honoring Civil War and Spanish-American War soldiers and about 150 varieties of mature trees.
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Every July, Bushnell Park plays host to the one of the best music festivals in the entire state.
Founded by Hartford jazz fan Paul Brown in 1992, the festival attracts jazz lovers to free concerts in the park every summer for decades.
All you need to enjoy the music at the Greater Hartford Festival of Jazz is a lawn chair, some sunglasses, and maybe a picnic.
Bushnell Park includes sweeping views of the State Capitol Building, especially from the Corning Fountain.
With its resplendent gold-leaf dome and Gothic-style turrets, Connecticut’s State Capitol building looks more European than American. Telling a visitor that it’s either a castle or European legislative building would be more than believable.
The State Capitol was constructed in the 1870s at a cost to taxpayers of a hefty $2.35 million (in 1870s money). This architectural marvel opened to the Legislature in 1878 covered with various statues and carvings covering the outside.
But inside is just as interesting, and free to take a tour of sights such as:
Walk across the street from the State Capitol to the former State Library and Supreme Court building. Built in 1910, the building has been beautifully restored and now holds the Museum of Connecticut History.
This small but interesting museum highlights Connecticut’s industrial, governmental, and military history.
Historical documents housed at the Museum of Connecticut History include:
Colt firearm enthusiasts will find its collection of early prototypes, factory models and experimental firearms stunning.
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Some other cool collections include Connecticut artifacts from the various wars the state and colony was involved in; and Freedom Trail quilts, telling the story of African-Americans in Connecticut.
Head west from downtown Hartford towards the posh neighborhoods near West Hartford.
Down the street from Mark Twain’s home here, across from Aetna’s headquarters, sits another throwback from Eastern Europe.
Here, this free historic attraction is more inline with Soviet architecture.
The original Cathedral of St Joseph was finished in 1892 with twin Gothic towers to mimic Montreal’s Notre Dame.
During morning Mass on New Year’s Eve, 1956, a fire erupted and spread to the wooden ceiling. According to church history, all that remained by the afternoon was “a charred, smoldering, ice-encrusted ruin.”
Almost immediately, the Archdiocese of Hartford commissioned a new cathedral. And they hired Eggers & Higgins of New York, more known for such impressive stone civic buildings and memorials as the Thomas Jefferson Memorial than churches.
But their design created a truly unique monument to Post-War Catholicism.
The Archdiocese consecrated the cathedral the same month that America imposed an embargo on communist Cuba and John Glenn became the first American to orbit the Earth.
The cathedral, made of concrete and limestone, soars 281 feet into the air. The front includes a massive sculpted frieze of St Joseph surrounded by the people.
While the exterior is intimidating, the gorgeous interior features one of the best examples of modernist ecclesiastical art in America.
Sunlight transforms as it enters the church through multi-colored panels of stained glass friezes crafted in Paris that reach almost 70 feet in height and surround the space.
The largest ceramic tile mural in the world sits behind the altar, depicting Christ in Glory.
Catholic or not, this cathedral is worth a visit, if only to admire the splendid result of an architectural gamble.
Listed on the National Register of Historic Places, the Governor’s Mansion has been the home of governors and their families since 1945.
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The mansion was first built in 1909 in the Georgian Revival Style, and an hour-long guided tour of the interior and outdoor sculpture garden is free on Tuesdays.
Visiting the Governor’s Mansion when it’s bursting with Christmas trees, poinsettias, wreaths, and more holiday decorations is an annual tradition on the list of best things to do in Connecticut in December.
Down the street from the Governor’s Mansion sits a true gem in this posh neighborhood close to West Hartford.
Opened in 1904, Elizabeth Park is America’s oldest public rose garden, and its first municipal one. With 15,000 rose bushes of 800 different varieties in magnificent formations, it’s easy to feel lost in an Elizabethan English rose garden, or somewhere more Continental.
Peak for this popular free attraction is early June, when the sight of blooming roses peaks and the air is heavy with their fragrance. But a visit here any time of year is one of the best date ideas in CT.
Other gardens include a wildflower trail, pond, sports and concert facilities, even herb and vegetable gardens.
This gorgeous park can help to better understand why Theodore Wirth, founder of the garden, believed that, “Roses bring joy to the public.”
Head west of Hartford (or north from southern Connecticut) to find even more free things to do in Connecticut.
After reading a few of the other entries of this list of free things to do in Connecticut, you may have gathered that Connecticut was a heavy-hitter in America’s industrial age.
And no city was more important in the era of American manufacturing than New Britain.
As the New Britain Industrial Museum explains, “out of the blacksmith forges populating 18th-century New Britain grew five major industries that fueled daily life in America for most of the 20th century. From the lock on your front door and the key in your pocket to the appliances in your kitchen and the parts in your car, all of those things and more were either made in New Britain, contained New Britain parts or were made on a New Britain machine.”
This free museum honors New Britain’s major contribution to the American economy with permanent and rotating exhibitions.
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Once you’ve finished with the well-preserved structure of Elizabeth Park’s Rose Garden, drive westward to the West Hartford Reservoir.
West Hartford’s Reservoir features paved trails along beautiful stands of trees and several different reservoirs. The longer of the two main loops is about three and a half miles. Either is ideal for any mobility level for running, walking, or biking on the marked bicycle lane.
While Talcott Mountain State Park isn’t ideal for all mobility levels, the steep uphill trek from the parking lot to Heublein Tower is worth it for those able.
The one and a quarter mile trail brings you to the 165-foot tower, the Heublein Tower. Gilbert Heublein, which is pronounced HIGH-bline, built the tower in 1914. Mr Heublein had promised his fiance that he would build a castle there, decades earlier, and once he made his fortune in Hartford, he did so.
The tower is a throwback to Heublein’s native Germany, architecturally speaking. And the top story is an observatory with panoramic views on a clear day of the Berkshires, Mount Monadnock in New Hampshire, and Long Island Sound to the south.
The view is what puts this free Connecticut attraction on our list of the best hiking trails in Connecticut, as well.
As weird as it is to admit, I’m a flower bridge snob.
The best one I’ve seen is the Bridge of Flowers in Shelburne Falls, Massachusetts.
But Simsbury’s Drake Hill Flower Bridge is a close contender.
This former railroad bridge was decommissioned and the local horticultural society installed plantings all along the bridge over the Farmington River.
Added benefit is that this bridge is within walking distance of downtown Simsbury, a town that feels like it’s the set of a Lifetime movie.
With elegant, historic charm, Connecticut is an ideal escape for couples to fall in love. Our list of the most romantic things to do in the state.
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Are you searching for romantic things to do in CT in a hurry?
No worries, we’ve all been there.
Having been in your shoes before, we pulled everything we know about planning and enjoying romantic activities across our state into one helpful and as concise as possible place.
This guide to romantic things to do in Connecticut includes everything you need to know:
Sounds good to you?
Then read on.
But first, a confession.
This entire guide developed during the largely inauspicious Covid-19 pandemic.
How so?
Well, when Connecticut shut down due to the statewide Covid quarantine lockdown, all the more typical romantic activities came off the list.
Romantic activities like dinner and a movie, museums and art galleries, even getting drinks at a local bar became risky, if not impossible.
But that meant that instead planning a weekend in Connecticut of romantic activities during Covid required more research.
And there was plenty of time to be had during the lockdown and afterwards.
Instead of the typical date night ideas, we found plenty of romantic activities to keep us busy.
A romantic weekend in Connecticut consisted of a lot of free attractions and activities, including:
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All in all, it was a huge improvement over sitting isolated in your apartment all day.
Before the Covid pandemic, we were experts at planning romantic getaways in Greenwich, our hometown.
Our town, the southernmost in Connecticut jutting into New York, has a little bit of everything for visitors looking for romantic things to do in Greenwich:
Add fantastic restaurants and nearby concert venues for ample date night ideas in Greenwich, and planning a romantic getaway here is easy.
But during the lockdown, when even entering nearby New York State was considered verboten for a time, this writer got the opportunity to explore more of Connecticut.
Read our favorite date ideas in Connecticut for the full list, but to whet your appetite:
Speaking of which, exploring our charmingly quaint towns is one of the most romantic things to do in Connecticut.
While cities like Hartford and New Haven have their own appeal, many of the charming, cute towns in Connecticut are unlike anywhere else on the planet.
And if you plan well, they can be a very inexpensive way to enjoy your day. All you need to cover is gas and maybe a cup of coffee or a sandwich while you walk around a cute downtown or two.
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Many of the towns that make this list are more than just a pretty face, though. They host unique shopping, hiking, museums, and more to keep you occupied once you’ve finished wandering around main street.
By region, some of the most romantic places in Connecticut include:
For such a small state, Connecticut offers a lot of variety.
Case in point: its restaurant scene.
Any meal can be an amorous one at the top romantic restaurants in Connecticut. It’s more a matter of choosing the right atmosphere:
A good meal is guaranteed at any of these venues.
A few choice dining options scattered throughout the state include:
Enjoying that moment after filling-up on a good meal and winding-down before bed in privacy does require a bit of planning.
But fortunately, there are plenty of options for romantic getaways across Connecticut.
Just like with dining, it’s more about knowing what sort of atmosphere and amenities you want to enjoy than necessarily what location.
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Obvious exceptions being hotels, inns, and cabins overlooking the beach or water.
But many of the most romantic inns, hotels, even cabins feature the perfect combination of amenities for a romantic getaway:
Read our full guide to favorite cabins, hotels, and inns to plan a perfect romantic vacation, but some favorites include:
Any time of year in Connecticut features its own style of romance:
It’s a sad summer for a New Englander who doesn’t get on the water at some point in the season.
This classic date idea is a great way to spend a day in the sun with your partner! Whether you choose to simply soak in the sun’s rays, indulge in a romantic picnic, or take a boat ride, there are plenty of romantic things to do on CT beaches! Here are just some of the area’s most beautiful, coastal spots:
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If you’re in need of some alone time together, a private ride on a luxury yacht may be just what you need. Greenwich Boat Charters provides a variety of options including dinner and cocktail cruises, New York Harbor tours, leisure harbor cruises, and more! The lull of the waves and the stunning backdrop of a Greenwich sunset is the perfect setting for any romantic evening.
Another great option is the Thursday night cruise from South Norwalk to the Sheffield Island Lighthouse. The trip includes sunset views and a traditional clambake on the island!
Traditionally, fall is all about harvesting and celebrating before the winter.
Today, it’s also about bonfires and observing the changing fall colors.
Hop in the car or on the train and visit a cute town anywhere in Connecticut during peak fall foliage season. There are some fantastic fall foliage driving routes to explore.
You could also plan your trip around farm visits, like apple picking in Connecticut orchards.
Or, the best afternoon of all could be had at one of the many Connecticut fall festivals throughout the state happening on almost every fall weekend in a typical year.
Romantic getaways in the spring, summer, and fall are easy in Connecticut. Many visitors often overlook the splendor of a romantic getaway here in the winter.
And yet there are plenty of romantic winter activities, both indoor and outdoor, to enjoy during a typical Connecticut winter.
It’s the ideal time to enjoy indoor activities such as:
Or just get cozy by a fire with a good book.
You could also try your hand at a new winter sport or hobby, some popular ones in Connecticut include:
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Regardless of the temperature outside, there are a few romantic activities that are delightful regardless of when you partake.
One of the most romantic things to do in CT involves indulging in some of the area’s finest wines! The wineries list of the Connecticut Wine Trail is packed with stellar options for wine tastings, gorgeous vineyards, and ethereal sunset views! It’s impossible for us to pick favorites, but here a few to try during your visit anywhere in the state:
Spoken from experience, winter day trips in Connecticut risk having an awkward period between when shops and attractions close around 5 or 6 and when you’re actually ready for dinner.
Stopping-in to a brewery is a perfect opportunity to pause, have a seat in a rustic industrial ambience, have a glass of local beer, and an appetizer.
An hour later and you’ll be ready to take-on the evening!
And there are so many local breweries here that the Connecticut breweries scene competes with some of the more famous beer lover destinations in America.
While certain activities are stereotypically romantic, anything can be romantic depending on the company.
Well, almost.
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One of the best ways to be romantic is to plan a day or weekend that feels spontaneous yet somewhat organized.
So plan a quick romantic day trip around visiting some of the most romantic things to do in Connecticut. Be sure to download our free guide, that includes romantic attractions, activities, and restaurants throughout the state.
Or just head to our neck of the woods and enjoy the various romantic attractions and activities here in Greenwich, Connecticut.
Enjoy the surf, sun, and sand from our list of the best Connecticut beaches. Plan the perfect beach trip, from Greenwich to Stonington.
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Even before movies like Jaws, New England was known for its beaches. Though not necessarily Connecticut beaches.
To be fair, there’s a lot of competition in southern New England.
Some of the most well-known beaches and beach communities in the country, as well as some of the oldest, are here:
While not officially part of New England, nearby Long Island has even more beaches to which New Yorkers make annual pilgrimages.
This Connecticutian has never been to most of the above destinations.
And especially not in summer.
Better-known beaches in the area are typically crowded. And the traffic alone to get there on a peak summer day potentially ruins the beach getaway experience before you even arrive.
Besides, there’s no need to go so far.
Why?
The best Connecticut beaches offer a perfect escape when you need your summertime beach vacation fix.
While each beach has a different atmosphere, amenities, even entrance requirements; a little advanced planning is all you need to enjoy your day, stress-free.
Not sure where to start?
Then read on for our guide to the best CT beaches.
Connecticut has plenty of beachfront options along its 618 miles of coastline.
Some state-run beaches scattered throughout the state have lifeguards on duty during beach season, from Memorial Day to Labor Day.
Coastal beaches with lifeguards include:
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The inland beaches along rivers and lakes with lifeguards are:
But Connecticut beaches are much safer than ocean beaches for one major reason. The waves and tides on Long Island Sound are much calmer than oceanfront beaches.
So as long as you’re a strong swimmer and are willing to take-on some personal responsibility, you should be alright wherever you go.
But even beaches without lifeguards often require passes and entrance fees. With only 618 miles of shoreline, pricing is how capitalist Connecticut keeps beaches from being overrun with visitors in the summer.
Depending on time, day of the week, and location of the beach, parking fees can range from $10 to as high as $65.
Some beaches still offer free parking and admission, but the trade-off is no amenities, not even bathrooms and trash cans.
Wherever you go, plan ahead to know what to bring (or when to stop to use a bathroom before you arrive).
Even before the Coronavirus pandemic, it was hard to keep track of information like parking and fees for beaches across the state.
Then the pandemic hit.
But it’s not impossible!
Some helpful pages on Connecticut’s state website for information related to the beaches and parks include:
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Even before Covid, beaches often reach capacity during the summer. And as long as Covid remains a threat, occupancy is often limited well below official capacity.
Long story short, be sure to arrive early wherever you decide to go.
The Connecticut shoreline is lined with cute beach towns.
While each has its own unique flair, they all have a similar nautical charm endemic to anywhere on the New England coast.
Heading east from the New York state border to Rhode Island, or rather from Greenwich to Stonington, the best beaches in Connecticut are as follows:
Long before it was known for its hedge funds, Greenwich was a resort town for New Yorkers.
When the railroads first arrived here, some neighborhoods actually changed their names to make them more appealing to beach-going tourists.
For example, Old Greenwich changed its name to Sound Beach during tourism’s heyday here, hoping to entice train travelers to disembark on its main street while heading up the coast. They changed it again more recently to its modern, more staid, name.
Today, Greenwich still has three beaches easily accessible to visitors willing to pay the entrance fees:
While each of the Greenwich beaches have their own unique appeal, Greenwich Point Park is the most spacious. As such, it has both the longest stretch of sand, and the largest parking lot for extra capacity.
Read our guide to the beaches near Greenwich, CT, for more information on park passes, and the unique aspects of each of our local beaches.
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Alternatively, skip the planning and book our Connecticut beach vacation package to enjoy a stay at our Connecticut bed and breakfast, plus a day at the beach.
Head further east along Interstate 95 (or officially, north-bound) to reach the next town on this list, Darien.
This next affluent Connecticut Gold Coast town features two beaches:
This 22-acre park features a sandy beach as well as other amenities, including: restrooms, tennis courts, public grills, and picnic areas.
Pear Tree Point Beach is actually two beaches of an 8-acre park at the mouth of Goodwives River.
Besides the beaches, other amenities here include public restrooms, and shaded picnic areas with tables and grills. There’s also a concession stand, so you don’t have to bring your own lunch if you’re so inclined.
This beach even has a boat launch and rock jetty if you want to launch your kayak or similar watercraft.
The major drawback to each of these beaches is the expense. While park passes are not inexpensive to access Greenwich beaches, Darien’s park entrance fees are even higher.
Norwalk has long had ties to the sea.
In fact, its nickname of Oyster Town stems from its position as a top producer of oysters.
Norwalk, despite its industrial, factory-town side, has always had more of a beachtown feel to this writer.
Between such local longtime fixtures as:
It’s still easy to feel the nautical side of town.
And true to its nature of being more middle-class in nature than its surrounding neighbors, Norwalk’s beaches are more accessible.
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Norwalk’s premier beach stems from its use in the 1600s. Early European settlers used the areas to graze their livestock, as it was easy to enclose.
Calf Pasture features three quarters of a mile of sandy coastline, and is easily accessible by car. The parking fee is lower than surrounding areas, and is even lower for guests arriving after 5 pm.
You could even walk from the East Norwalk train station if you’d rather spend about 40 minutes walking than the $5 cab fare or parking fee. Entry to the beach is free, provided you arrive car-less.
Besides a sandy beach, other facilities include:
Literally right next to Calf Pasture Beach (and yet they’re different parks) lies Shady Beach.
Although a bit rocky, Shady Beach features lovely views of Long Island Sound.
The grassy area has grills and picnic tables for barbecues, and lifeguards are on duty in the summer months.
Parking can be a bit tricky, though, so be prepared.
Westport is the most avant-garde of the towns along the Connecticut Gold Coast.
But several of its neighborhoods are ideal beach towns.
So perfect, in fact, that the state picked this town as the site of the first state park. A commissioner determined that an island off its coast was perfect for a shore park after exploring the length of Fairfield County’s coast.
Westport’s town beach sounds more like a destination in the Caribbean.
But the beach itself is a gorgeous New England spot, prime for photos of sunsets over the Sound or the boats of the marina.
This 29-acre park sits on the Long Island Sound at the mouth of the Saugatuck River.
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Bathrooms, lockers, and a well-stocked concession stand are available to guests. There’s also a boardwalk and pavilion for guests to check-out while they’re enjoying a day at the beach.
As is the case with every beach mentioned so far, there is a fee to enter the park. In this case, only a parking fee is required, serving as an entrance fee as well.
The state did, admittedly, pick a great location for a state beach.
Beyond the beach is a range of woodlands and wetlands to explore on the various hiking trails. The western side of the island has oak forests and a small observation deck overlooking the marsh trails lining Sherwood Millpond. The Tidal Marsh Nature Trail sits to the east of the island, as well as the Nature Center.
But the biggest draw to Sherwood Island is, of course, the beach.
One of the most unique features of the beach is the three-color sand. Added to the more typical cream-colored sand is red and black sand, from garnet and magnetite, respectively.
The minerals separate with the tides, creating beautiful stripes in the beach.
This 238-acre expanse of a park is worth a visit, regardless of the time of year.
Just to the east of Westport (and one of the oldest settlements in Fairfield County), Fairfield has won awards for a high quality of life.
And one of the major benefits of living here are its beautiful beaches.
Like most CT beaches on this list, Fairfield beaches require entry fees for non-residents in peak beach season.
Check the Town of Fairfield’s website for more information regarding seasonal stickers and daily parking fees.
Open from Memorial Day to Labor Day, Penfield Beach’s amenities include concessions, a picnic area with public grills, a playground, and restrooms.
Just off of Interstate 95, Jennings Beach features 27 acres of sandy beach and gorgeous views of Long Island Sound.
If you can make it here during the week in the summer, parking fees are significantly lower.
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Lifeguards are on duty here in the summer, and staff offer swimming lessons. Other amenities include:
In the winter months, Jennings Beach is also one of the most dog friendly places in all Connecticut.
A majorly influential Connecticut city in the 19th Century, Bridgeport has fallen on hard times over the past century due to corruption and mismanagement.
But the vestiges of that gloried past makes Bridgeport an interesting place to visit, especially for visitors interested in industrial architecture and the romance of a place past its prime.
Pleasure Beach is one of those fascinating places, with an entire resort town on an island off the coast falling into decay. But as it’s less easily accessible, via only a ferry from Bridgeport or a mile walk from Stratford, this writer didn’t include it in this list.
P.T. Barnum of circus fame loved Bridgeport passionately. So much so, that he served as mayor and donated his collection and extensive land to the city for parks and museums.
His contributions, like his museum and Seaside Park, are a major reason why Bridgeport is on the list of Fairfield County destinations.
Open for swimming from Memorial Day to Labor Day, Seaside Park Beach is an expansive park with many of its grandest features still visible.
Beachgoers can pay for day passes that are lower than many of the other surrounding towns.
Many of the amenities here are typical of Connecticut beaches:
And yet this beach features more unique, and grander, touches, such as:
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Like Greenwich, Stratford offers forests and hills for hiking inland, beautiful beaches along the shoreline, and a cute downtown in-between.
Unlike Greenwich, Stratford has a reputation for having a more moderate cost of living.
The neighborhood of Lordship, separated from the rest of town by an airport, industrial complexes, and marshes is the epitome of beach towns.
Of the several beaches along Lordship’s coast:
Short Beach is most appealing for its view and accessibility, situated at the mouth of the Housatonic, looking across to Milford.
Handicap access is available at the northern end of the beach. Picnic areas and a playground are at the southern end of the beach. Guests will also find a concession stand and showers operating on the beach in the summer months.
Milford is another one of the charming Connecticut towns lining the coast.
While you wouldn’t guess it from the view along Interstate 95, Milford has both a cute downtown and several beach neighborhoods.
Walnut Beach is a well-established beach community in Milford, and its eponymous beach is quite pleasant.
In a typical year, Walnut Beach hosts a summer art festival and concert series for visitors and locals.
While Walnut Beach is free for Milford residents, this beach also charges a parking fee for non-resident visitors arriving between Memorial Day and Labor Day.
Walnut Beach and Silver Sands State Park are connected by a mile of wooden boardwalk.
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Silver Sands State Park is another massive state park, with 297 acres of dunes, salt marsh, woodlands, a beach, and Charles Island.
Charles Island, accessible at low tide from the shoreline, is known as the “thrice cursed island”. Legend has it that Captain Kidd buried a treasure here before traveling to Boston, where he was captured and executed. The treasure is supposedly cursed, and despite many attempts to locate it, has yet to be found.
The island also bears ruins of a resort from the 1800s, as well as a chapel from a religious retreat that occupied the island in the 1930s.
Today, it is an important nesting ground for several species of sea birds. The interior of the island is closed to visitors from May 1 to August 31, to leave the nesting birds undisturbed.
Visitors can still visit the shore of the island, though be aware of the tides when crossing the half-mile long sandbar. The isthmus is slippery, even at its driest, and it submerges quickly.
Back on the mainland, Silver Sands State Park is lined by a three-quarter mile wooden boardwalk. Unique to most of the parks on this list, until recently there was no parking fee.
But those days are gone, after the state invested in adding new amenities to the park, like restrooms.
That said, the parking fee is reasonable.
Lifeguards are on duty at the park from Wednesday to Sunday in the summer months.
As the name implies, West Haven is just to the west of New Haven.
It is home to 4 miles of publicly accessible beach, 25% of all public beaches in Connecticut.
All the beaches in West Haven are open to the public from 9 am until dusk each day. Lifeguards are on duty from 10:15 am to 3 pm:
Non-residents pay a daily parking fee from Memorial Day to Labor Day.
When a pandemic is not posing a health threat, at least.
This small, sandy beach is the western start of West Haven’s string of beaches.
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Facilities at Bradley Point Park include a volleyball court and portable toilets.
A walkway runs parallel to Long Island Sound starting at this park. The walkway is ideal for pedestrians, cyclists, and rollerbladers; with sweeping views of Long Island Sound along much of the way.
It connects all of the parks together, from west to east:
The eastern terminus of West Haven’s line of beaches, Sandy Point Beach made the Boston Globe’s list of the best beaches in New England in 2018.
To be fair, this beach won the accolade for the birding opportunities, as an important breeding ground for shorebirds.
But any of these beaches are great. If you’re a birder, this beach just has one extra reason to visit.
Every town from New Haven to the Connecticut River has their own public beach to go with their cute, historic yet beachy downtowns.
Across the harbor from West Haven’s beaches, Lighthouse Point Park feels like Seaside Park in Bridgeport: as in, it’s seen better days.
But that adds to the charm of this park, with:
As should come as no surprise, there is a parking fee for non-resident visitors. Check New Haven’s website for more information on parking fees.
This beach is not very well-known, which adds to its charm.
Jacobs Beach is just off of Seaside Avenue in Guilford.
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For the cost of a daily pass for non-residents (season passes are available to Guilford locals), visitors can find typical Connecticut beach amenities:
And 25 acres of parkland and sandy beach, ideal for kayaking.
This park is the largest in the entire state.
Hammonasset Beach State Park stretches over two miles along the coast of Long Island Sound.
It’s also one of the most developed, with ample parking, a boardwalk lining much of the beach, and concession stands and picnic areas.
With over 500 electric and primitive camping sites, this park is popular with campers, as well.
Dogs are even allowed in the picnic area of the park year-round, though not on the beach.
And last but not least, a designated car-top boat launch area makes kayaking here easy to do, as well.
Open for swimming the third weekend in June through Labor Day weekend, Clinton Town Beach is about a ten minute drive from Hammonasset.
Facilities here include:
As with every other beach so far, access in the summer is restricted to residents with a beach pass or non-resident visitors willing to pay the town’s parking fee.
The stretch of Connecticut shoreline from Old Saybrook to Rhode Island is the center of summertime tourism in the state.
This writer spent many summers on Groton beaches as a child.
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Katharine Hepburn’s old haunts have been a draw for visitors from New York City for about a century.
One of the major draws has always been its shoreline. Its arts and culture scene has recently served as icing on the cake.
Harvey’s Beach offers 100 yards of beach, with low parking fees.
Amenities here include:
Harvey’s Beach also hosts events and special activities throughout the summer, such as:
But the beach and views of the surrounding coastline are a draw in and of itself. The sunsets over the coast and Long Island Sounds from here are definitely Instagram-worthy.
Across the Connecticut River from Old Saybrook is Old Lyme.
Like Old Saybrook, this has been a resort town for the better part of a century. Like Greenwich, Old Lyme was the site of an Impressionist Artist colony in the early 1900s.
Sound View Beach in Old Lyme puts a lot of effort into attracting visitors to its beach.
Some of the more unique beach amenities close to if not right on the beach include:
This is the only Connecticut beach that even has its own craft beer.
Some of the public events that are major draws in typical summers include:
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One of the amenities not available at this beach is the presence of lifeguards.
To access the beach, non-residents can use (and pay for) parking at private lots, a town parking lot, or street parking. Parking fees are payable at kiosks.
Check the Sound View Beach website for more information regarding fees and events.
Niantic, like Old Lyme, is the epitome of a beach town.
This cute little town is popping in the summer months and quiet in the winter. The town and its beaches are easily accessible to both the train station on the main drag and I-95.
Rocky Neck State Park is a 708-acre park of varying terrain and interest:
Facilities here are centered at the West Beach:
Camping areas and hiking trails meander throughout the park.
Closer to Niantic than the rest of East Lyme, Hole in the Wall Beach is part of McCook’s Point Park, a 62-acre park centered on a bluff overlooking Niantic Harbor.
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Compared to McCook Point Beach a little further west, Hole in the Wall Beach has the better name. It derives from the tunnel entrance under the train tracks that gives the town of Niantic access to this little beach.
While this park is open year-round, visitors need a pass to access the beach from Memorial Day to Labor Day, when lifeguards are on duty.
Unique to many of the parks on this list, Hole in the Wall beach allows dogs, provided they’re on a leash at all times.
Restrooms and foot-washing stations are on the town-side of the tunnel.
On the western side of the McCook Point Bluff is the McCook Point Beach, which has a boardwalk, walking paths, a picnic area, and yet more restrooms.
Close to Harkness Memorial State Park, Waterford Beach Park is a quarter mile of sandy beach.
It’s actually one of the only unmodified, natural beaches in the state, and features an intact dune system, sandy hills, and tidal marshes.
Amenities here include:
Non-residents can purchase a daily parking pass at the entrance to the beach. But parking is limited, so plan to arrive early.
Just across the Alewife Cove from Waterford Beach is Ocean Beach of New London.
National Geographic voted Ocean Beach as one of the best beaches in New England.
This park is more like a vacation resort, with more amenities beyond its half-mile, white sugar sand beach. Major attractions include:
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The park hosts live entertainment and weekly events on the Boardwalk Stage, including:
Ocean Park is open each year from Memorial Day to Labor Day. Ocean Park admission is parking for one car, up to five people per vehicle; or a per-person walk-in rate.
This small beach is the only public beach in Mystic.
The beach strand at Williams Beach Park is only 120 feet long. And while parking is free, there is no lifeguard on duty.
Stonington, an old whaling town just east of Mystic, is worth a visit any time of the year.
And beach goers can lump a trip to the beach onto their visit with a trip to DuBois Beach at the tip of Stonington Point.
Lifeguards are on duty in the summer, but visitors are encouraged to donate to help maintain the beach. Parking is free, but very limited, so arrive early.
Heading to town for lunch or shopping?
Then be sure to use the facilities before returning to the beach, as there are no restrooms here, either.
This best of the Rhode Island beaches is close to the Connecticut border, across the Little Narragansett Bay from Stonington.
Misquamicut State Park is similar to Ocean Beach Park in New London in being an attraction in and of itself.
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If its seven miles of sugar white sand and clear water aren’t a draw in and of themself, then other amenities should more than suffice.
The park’s bathing pavilion is a structure reminiscent of a small beach village. It features several buildings including a bathhouse, gazebos, concession stand, and gift shop.
Even more shops, restaurants, and water sports equipment rentals are a short walk back to town in Misquamicut.
Lifeguards are on duty from 9 am to 6 pm during the summer, and the park hosts two annual music festivals: Springfest and Fallfest.
There's more to Mystic than Mystic Seaport & Mystic Aquarium! Check out our list of attractions, activities, and things to do in Mystic, CT.
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It seems as if everyone and their mom knows about Mystic, Connecticut.
The fact is:
Everyone has heard of Mystic because there are so many things to do in Mystic, CT.
While Mystic Pizza bears some responsibility for its fame, the movie producer only got the idea while visiting Mystic in the first place.
Mystic is New England’s answer to other tourist traps in America:
But, as is typical of a state that peddles historic charm, Mystic, CT, is a tourist destination that oozes class, elegance, and charm.
Many of the activities, attractions, and things to do in Mystic, Connecticut, focus on the old industries of whaling, shipbuilding, and anything maritime.
But there’s plenty more to explore close to Mystic. Much of the surrounding farm and woodland is still intact, unique to Connecticut, so vineyards, hiking, and farm visits are an option here.
And there’s still a bit of kitsch to be found, if that’s what you’re into.
Ready to plan your visit to Mystic? Read on.
With so much to do in Mystic, first-time visitors need a quick list of the attractions that everyone seems to do here.
The majority of these attractions are centered around the Mystic River.
The source of this mysterious name is a Pequot term, “missi-tuk”. The term translates to a large river whose waters are driven into waves by tides or wind.
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Before the arrival of tourists, Mystic was one of the pre-eminent shipbuilding centers in America. Various shipyards along the Mystic River built over 600 ships during a 135-year period starting in 1784.
Ten years after shipbuilding ceased, aficionados founded what is now one of the largest maritime museums in the country in 1929.
The museum hosts:
But one of the most unique draws of Mystic Seaport Museum is the four National Historic Landmark vessels, including the second item on this list, the Charles W Morgan.
The Charles W Morgan is the only wooden whaling ship still in existence. It also bears the title of being the oldest still floating commercial vessel in America.
It’s permanently docked at Mystic Seaport, where it can’t hurt any more whales.
After an extensive refit, visitors can explore the ship to learn more about the whaling lifestyle of the 1800s.
Whale oil was immensely valuable before the widespread use of oil extracted from the ground, and whalers lived a hard life to acquire it.
Visit the ship after reading Moby Dick, then see how cramped of a space the crew endured all to enable a ship captain to pursue a dangerous obsession.
Speaking of which, this ship was built for the average height of the 19th century, so watch your head down below!
Not into learning the history of mankind’s efforts to exterminate what’s left of the world’s megafauna?
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Then head to the second major attraction built in the Mystic area to keep you occupied: Mystic Aquarium.
This attraction even hosts living whales, of the beluga variety.
Many of the exhibitions are outside, including the belugas and other creatures:
But a visitor could knock all of these off their list in about 30 minutes if the weather is uncooperative.
Inside exhibits include more of the typical aquarium fare:
While this aquarium is fairly small, it is heavily involved in the work of researching, preserving, and protecting the life of our oceans.
So, there’s no guilt in supporting their mission.
Speaking of small attractions, the Mystic River Bascule Bridge is cool, but not something that will take-up most of your afternoon.
This unique swing bridge follows a similar construction to more famous drawbridges, like the London Bridge.
In the warm months, this bridge lifts every 40 to 60 minutes for boat traffic, so there should be plenty of opportunities to see the bridge in action while visiting the surrounding downtown.
Historic Mystic, straddling the eponymous river, exudes quaint charm.
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Downtown Mystic is walkable and full of small stores, restaurants, and specialty shops. Some of the most popular ones here include Bank Square Books and the Mystic Army Navy Store.
Mystic’s waterfront park is an ideal location for people watching, or to see the Bascule Bridge in operation.
And yet the main attraction is the architecture of the buildings along Main Street itself. Much of the quaint fishing and whaling village has survived to the present day, and walking around town is a top free attraction here.
On the edge of downtown Mystic, overlooking the Mystic River, the Mystic Museum of Art is rapidly developing into an attraction in its own right.
While this charming art gallery is petite, the art exhibitions change every few months and display in a gorgeous space festooned with plenty of natural light.
The surrounding manicured gardens are also lovely. Besides, entrance is free, so the only cost of a visit is your time.
An artist colony started the Mystic Museum of Art in 1913, and visitors can participate in one-day art workshops or children’s art classes.
Outdoor malls are fairly commonplace anywhere in the States. But where else can you find a recreated 18th-century New England village while finishing your Christmas shopping?
The charmingly quaint feel to the uniqueness of this shopping center makes it one of the most unique things to do in southern Connecticut.
The range of shops include:
And the experience of walking around is just as pleasant. The owners of the development included such period features as:
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And the entire outdoor space is dog friendly, which also lands this spot on our list of the most dog friendly places in Connecticut.
Just be sure to keep your pet away from the ducks.
This nature center has been providing guests the opportunity to experience local flora and fauna first hand for nearly 70 years.
A few of the attractions on-site include:
And yet one of the most unique and mysterious attractions is a nearby archeological site that Denison Pequotsepos Nature Center has exclusive access to, as caretakers of the land.
Gungywamp is an exceedingly confusing site, with artifacts scattered throughout the 100-acre space.
Some of the major things to see at Gungywamp include:
Due to regular settlement and re-settlement throughout recent history, the site has likely been arranged and rearranged multiple times.
Hence the perennial frustration of archaeologists studying the site.
Across the road from the Denison Pequotsepos Nature Center sits an opportunity to experience yet another piece of 17th century history.
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While the inside is interesting, with friendly staff in period dress sharing stories from the house’s long history, the views alone are worth a visit.
Especially in April, when bright, yellow, daffodils surround the Denison Homestead.
Like other historical attractions on the East Coast:
Mystic appears to have a larger amount of paranormal activity than the average town.
Or at least better documented ones, for the sake of providing fodder for walking ghost tours of one of the most haunted places in Connecticut.
Whether you believe them or not, ghost stories are a fun way of learning about the local culture: what terrified and mystified locals. It’s also interesting to consider what legends were important enough to keep alive to the present day.
And the Seaside Shadows Downtown Mystic tour is the top walking ghost tour in Mystic.
Connecticut native Courtney McInvale Reardon guides guests on a tour past local Mystic haunts by lantern light.
Spend an evening learning about the events from the 1600s to the present that developed into the best known spooky tales today.
With the top attractions on your list for your upcoming visit to Mystic, round-out your trip with a few free activities.
Or perhaps you’re planning a more romantic Connecticut getaway?
Either way, this guide has you covered, plus top Mystic restaurants.
While visitors don’t equate charming Connecticut with being inexpensive, the most charming towns in Connecticut all feature free things to do.
In fact, more than a few of the top Mystic attractions are free to visitors:
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Some extra free things to do in Mystic, CT, include:
This beautiful cemetery is a short drive away from downtown Mystic, and up the road from Mystic Seaport.
Elm Grove Cemetery is a picturesque work of the Victorian era. It was built during the Rural Cemetery Movement.
The movement created park settings of rolling hills, brooks, and trees. And visitors to Elm Grove Cemetery can still admire the flowers, willow trees, crowns, and trumpeting figures decorating the ornate sepulchers.
The impressive granite memorial arch was an 1890s addition to the entrance.
Today, the park-like atmosphere is worth at least a drive, or better yet a walk, on a nice day. Even those wary of the deceased will appreciate the gorgeous views of Mystic River.
This is admittedly not much of a destination.
But it is a nice place to take a break while wandering around downtown Mystic. The square is at the intersection of Holmes and East Main Street just before heading west across the Bascule Bridge.
The Liberty Pole Square features a large anchor seated on a gray, round, brick platform.
Surrounding the platform is a three foot high stone wall with flat slab stones for sitting and admiring.
The town dedicated this monument to the citizens of Mystic River Valley, who hold in their hearts the precious gift of Liberty.
Thanks to traffic lights, crossing Main Street to appreciate this dedication to liberty may prove a bit difficult.
Enjoy some surf, sand, and even a sunset depending on when you visit Williams Beach Park.
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This little beach, only 120 feet of shoreline, is the only beach in Mystic proper.
And parking is free, though be prepared to go elsewhere for typical beach amenities like lifeguards and bathrooms.
Some more of the best Connecticut beaches are just a short drive from Mystic, however.
With attractions like Mystic Aquarium and Mystic Seaport, visitors sometimes give this town a reputation for being just a family destination.
And while it is, a trip here can also be decidedly romantic.
100 panoramic acres bordered by tidal marshes, vistas of Long Island Sound, and a cove await at Saltwater Farm Vineyard. The 15 acres of vineyard are planted with six grape varieties, with a popular tasting room on-site.
This top pick of the Connecticut wineries honors its place in Stonington history as coastal Connecticut farmland and a private airport dating from the World War II era.
Regardless of when you visit, you may be so enchanted by this place that you will be planning your wedding here.
This waterfall is a bit of a drive inland from Mystic, in Norwich, Connecticut.
And while the hometown of Benedict Arnold may not be on the top of your list, this is a sweet place to swing-by if you happen to be in town.
Yantic Falls features an easy quarter of a mile trail to a beautiful waterfall, along with a rustic pedestrian bridge, old railroad bridge, and mill buildings converted to apartments.
Legend has it that Yantic Falls was a favorite camping and battleground for the local Mohegan tribe. In the 1640s, Uncas, Sachem of the Mohegans, led his tribe in battle against the rival tribe of the Narragansetts. Members of the Narragansetts chose to leap to their deaths in the chasm of Yantic Falls than surrender.
The modern falls are part dam and part natural, with a main plunge of 40 feet in height. After the falls, the Yantic River continues through one of the most impressive gorges in the state.
The best time to see the falls is in the winter, when mist freezes on the trees and the water freezes solid in cascades over the rocks.
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This little island off the coast of Mystic is one of the most unique places in all of Connecticut.
Owned by an organization of Catholic monks, this little island offers a serene and peaceful escape from daily life.
The gardens and sweeping views of Long Island Sound make for a pleasant way to pass an hour or two.
And everything from parking to wandering around is free, as well. That’s why it’s also won the title of one of the best free things to do in Connecticut!
This vineyard is another popular spot for locals, especially for the free concerts on the lawn held each summer.
On a warm afternoon, you’re sure to find plenty of people sitting outside enjoying wine and the gorgeous views, live music in the tasting room, and smiles all around.
On the southern end of a peninsula jutting south from nearby New London sits a beautiful turn of the 20th century former estate.
Harkness Memorial State Park features Eolia, a 1906 Roman Renaissance Classical Revival-style mansion. The 304-acre property belonged to philanthropist Edward Harkness before reverting to the state’s care.
The elegant summer getaway for the Harkness family includes over 230 acres of sweeping lawns, stately trees, charming gardens, and plenty of space to spread-out.
You’re sure to see more than a few locals taking their engagement photos here.
After spending the day exploring one of the largest maritime museums in America, a relaxing cruise aboard an old sailing ship, watching the sunset, seems ideal.
The Argia, an 81-foot traditional sailing vessel, will take you past the islands and lighthouses of Long Island Sound, and give you plenty of fresh air.
The cruise takes about two hours, exploring Fishers Island Sound, then Noank and Groton Long Point. And while a sunset cruise sounds the most romantic, others throughout the day will provide just as interesting an experience.
Just be prepared for a bit of challenge with parking, as the dock is close to the Mystic Bascule Bridge.
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Another local option is Poet’s Lounge Sailing Charters.
Like anywhere else in Connecticut, Mystic is particularly charming in the Fall.
And one of the most romantic attractions to visit during Fall in Connecticut is without question the B.F. Clyde’s Cider Mill.
This attraction, a short drive from Mystic, is the last steam-powered cider mill in America. It earned National Mechanical Engineering Landmark status in 1994.
Be sure to visit on weekends, when the cider mill is operating.
But any day is an opportunity to enjoy the cider, which many claim is the best you’ll ever have. And other unique things to try include:
The cider mill is a great stop either heading to or from Stonington, the next romantic spot on this list.
Mystic is actually not a real town.
The village is split between two nearby towns, Groton and Stonington.
And little Stonington, perched on a peninsula jutting into Long Island Sound, is worth visiting on its own.
A quaint holdover from when this area was heavily involved in the 19th century whaling industry, downtown Stonington features a tightly-packed village of houses of varying architectural styles from its heyday.
While many visitors have come to town to experience Mystic Pizza, there’s much more to Mystic and the area than one pizzeria.
The pizzeria on which the movie is based has long closed, by the way, though there is another Mystic Pizza to visit for Julia Roberts aficionados. TV screens inside show the movie all day, every day.
Seafood and yes, Italian, are major dining mainstays here. Below are some top picks:
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This upscale restaurant is right off of the waterfront in Mystic. Anthony J’s Bistro specializes in Italian and seafood with a cozy ambience.
The historic clapboard house provides a rustic yet chic venue to try the age-old aphrodisiac. If oysters don’t do it for you, there are plenty of other dishes to choose from. All include ingredients from local farmers and fishermen.
After dinner, enjoy the open air, romantic views of downtown Mystic, and a drink, at the Treehouse, the outdoor deck and bar attached to the Oyster Club.
This restaurant has racked-up plenty of accolades and awards since opening in 2011, including from Travel + Leisure, Connecticut Magazine, and Town and Country.
This trendy Italian eatery is situated in the Whaler’s Inn in downtown Mystic. Bravo Bravo prides itself on serving modern seaside cuisine with an Italian twist, like its signature osso bucco. Save room for one of their decadent desserts!
If looking at live fish all day gives you seafood munchies, Go Fish Restaurant sits across the street from Mystic Aquarium in the Olde Mistick Village shopping center.
As the name suggests, this spacious and colorful spot is a go-to for seafood, including its sushi bar.
This stylish yet affordable option in downtown Mystic offers traditional New England dining. And yet the biggest draw is its extensive kids menu, making S&P Oyster Company one of the most kid-friendly restaurants in Mystic.
Connecticut Magazine awarded the Engine Room the accolade of Best American in 2019. This rustic restaurant offers a more casual atmosphere than its award would imply. The menu is full of mouthwatering burgers and sandwiches, matched by a lengthy craft beer menu.
Much of the menu comes from Stone Acres Farm in Stonington, much like Oyster Club and Grass and Bone.
Every town in Connecticut has at least one Mediterranean-style restaurant, and the Pita Spot offered the best Lebanese cuisine in the Mystic area.
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As of 2019, the Pita Spot has reinvented itself as Vivian’s Mediterranean Market, serving Lebanese and Italian fare prepared and packaged daily.
So you can still enjoy their cuisine, with your home, hotel room, or vacation rental as the venue!
Polished American cuisine centered on seafood is what draws diners to Red 36. What keeps them coming back are the waterfront views and the outdoor seating overlooking the harbor.
Connecticut magazine awarded this restaurant multiple accolades in 2019, for best outdoor dining and seafood.
Why skip your weekend morning tradition while on vacation!?
Rise is one of the newer restaurants on this list, but has already won recognition for being one of the best options for breakfast and brunch in the entire state.
The shop was started by a former Oyster Club employee. And its clam-shack vibe is perfectly appropriate, situated by the waterfront.
Locals are just as willing as tourists to wait in line to savor the coffee and baked goods at Sift Bake Shop. Owner Adam Young was the winner of the Food Network’s Best Baker in America title in 2018.
Pretty impressive, and likely explains why Sift also scored a place on Connecticut magazine’s list of best desserts in the state.
This combination butcher shop and sandwich shop started under the premise of making high-quality cuts of meat accessible to the general public. That way, you could enjoy restaurant-quality meat at home in your own cooking.
But the lunch sandwiches at Grass and Bone are pretty damn good.
A new addition to the roster of dining options at Whaler’s Inn, the Shipwright’s Daughter offers another swanky option to experience the local seafood.
The pork belly, roasted oysters, cod chowder, and lobster roll win plenty of praise from visitors.
This lobster shack is not in Mystic.
Company name
But Ford’s Lobster Restaurant is only a ten-minute drive away in Noank. And it’s well worth the trip!
The patio-only seating, waterfront views, and laid-back vibe alone make this place unique. But the simple yet stupendous menu includes fish tacos, lobster rolls, and higher-end options like roasted cod over mushrooms.
The most famous menu item is the Bisque Bomb, a half-pound of hot lobster smothered in lobster bisque, and all served in sandwich form.
The summer months, especially July and August, are busiest at Mystic.
But every time of year has its own appeal in Connecticut, and Mystic is no different.
Winter months mean fewer tourists, so everything from scoring tickets to finding parking is much easier.
Provided you’re not attempting to visit during or shortly after a snowstorm.
Most of the attractions that make Mystic so unique are still open in the winter. In fact, such a large number of indoor attractions or places still visitable in the winter make this one of the best choices for Connecticut winter getaways.
That's easy!
The first charming town you'll hit when you cross into Connecticut is going to be Greenwich.
We're the Gateway to New England for a reason.
Click below to download the free Greenwich Visitor's Guide. It's goes in-depth on the attractions, activities, and things to do in our posh, elegant, and very unique town.