As befits a quaint, little state, there are plenty of cute towns in Connecticut.
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.
But considering Connecticut’s location, there are plenty of easy day trips to take from the big city, whether that’s:
- New York City
- Or anywhere else on the East Coast
There are plenty of ways to prioritize exploring towns, a few that come to mind include visiting points along:
- The Connecticut Antiques Trail, or simply the most unique antique stores in CT
- A list of Connecticut breweries
- CT wineries on the Connecticut Wine Trail
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.
Want to know the cutest towns in Connecticut? Then watch our video. Afterwards, keep reading for the full list.
Read on for our list of our favorite cute towns in CT with the most charming historic Connecticut districts.
Cute towns in CT: Table of Contents
- Fairfield County
- Litchfield County
- New Haven County
- Middlesex County
- New London County
- Hartford County
- Cute towns in CT FAQs
22 of the Most Cute Towns in Connecticut, by County
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.
Map design by Stanton House Inn
Cute towns in Fairfield County, Connecticut
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.
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:
- Old Greenwich is our beach town
- Glenville is our former mill town
- Cos Cob is the artsy, funky, part of town
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 coastal Connecticut bed and breakfast inn 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
- Designer boutiques
- And art galleries
As well as some of the more quirky independent shops, holdovers from Greenwich’s less high-end days.
And the restaurants along Greenwich Avenue and around downtown Greenwich are splendid. And if you need even more options, head next door to the city of Stamford to enjoy their dining scene.
Thanks to advanced foresight and good geography, the town of Westport, CT, 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 (though nothing compares to the Greenwich real estate market).
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.
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. The main street, lined with historic buildings from the 19th Century, is a draw in and of itself.
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.
Cute towns in Litchfield County, Connecticut
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.
It’s also the land of covered bridges, or at least the ones closest to Greenwich.
But anytime of year is a good time to visit Litchfield County. Head up in the summer to take advantage of one of the last drive-in movie theaters in all Connecticut.
Cross the Housatonic River from the Danbury area of Fairfield County and enter into classic New Milford.
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.
It also bears the distinction for being 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. It’s one of the best state parks in the entire state of Connecticut.
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 the town of 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 West Cornwall, Connecticut.
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.
West 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.
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.
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.
Charming towns in New Haven County, Connecticut
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 entry on the list of cute, small towns in Connecticut to the east of the city, Branford. Or pause to explore all the unique attractions in New Haven, Connecticut, before continuing on your tour.
Up to you.
Branford has the largest piece of the so-far completed Shoreline Greenway Trail. The trail 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 Connecticut 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.
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.
Two waterfront locations to breathe the salty air of Long Island Sound 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.
Three Connecticut counties down, three to go!
Cute towns in Middlesex County, Connecticut
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:
- farm houses dating back to before the Revolutionary War
- 19th-century Federal style mansions
- The First Baptist Church of Essex, one of just three Egyptian Revival churches built in the entire USA
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.
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.
Darling towns in New London County
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 has heard of Mystic, Connecticut.
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. The seaport museum 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.
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:
- Mystic Pizza, made famous by the 1988 film starring Julia Roberts
- Mystic Drawbridge Ice Cream, sitting right by the famous Mystic Bascule bridge
Some other cool attractions, activities, and things to do in Mystic, Connecticut include:
- Taking a sail on the Schooner Argia
- Boarding the world’s first nuclear-powered submarine at the Historic Ship Nautilus & Submarine Force Museum
- Mystic Seaport hosts several holiday events. It’s one of the best places to visit in CT in December.
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.
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.
Hartford County’s cutest towns
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 places to see near Hartford, the state capital. 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 century
- 18th century
- And 19th century
Three buildings are even listed on the National Register of Historic Places, all fantastic examples of Colonial architecture:
- Buttolph-Williams House
- Joseph Webb House
- Silas Deane House
Fishing and boating enthusiasts will likely elect to skip the historic houses and head to Wethersfield Cove.
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.
Even More Cute Towns in Connecticut to Explore
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:
What are the cutest small towns in CT?
In no particular order, that would be:
What are some of the most artsy and funky towns in Connecticut?
Many of the towns on this list are mentioned above, but a few didn’t make the cut because they:
- Weren’t cute enough
- Were too big
- Or too pretentious to be considered cute
Not saying who.
But the most artsy and funky towns in Connecticut include:
- New Haven
- Old Lyme
- East Haddam
- New Canaan
- The Cos Cob neighborhood of Greenwich
- The Saint Mary’s by the Sea and Black Rock neighborhood of Bridgeport
When’s the best time to visit these cute towns in Connecticut?
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.
And springtime in Connecticut is fall in reverse, with the joy of knowing warmer weather is on its way.
If you’re planning a birthday, check-out our guide to the most unique adult birthday activities throughout Connecticut.
Plan a more in-depth visit to Greenwich, Connecticut, with our Visitors Guide to Greenwich. At the very least, you’ll have a solid plan for the first town you’ll be able to cross-off your list.
Updated and republished: July 28, 2022