View from Westport Bridge over Saugatuck River and architecture near downtown in Westport, Connecticut. Image credit Miro Vrlik Photography via Shutterstock

10 Adorable Small Towns In Connecticut

New England, encompassing six states, including Connecticut, is known for its old-world charm, clam chowder, and the US Constitution. Besides its historical importance, some of Connecticut’s greatest assets are its lovely small towns. Spend time walking down quaint main streets near the ocean and enjoy the natural beauty of the Constitution State. Many of the state's towns have a distinct seaside atmosphere and are excellent getaways. Regardless of the season, there are plenty of adorable small towns in Connecticut to explore.


Connecticut River in Essex, Connecticut and fall colors
Connecticut River in Essex, Connecticut.

In 1995, Essex topped the list in the second edition of Norman Crampton’s book The 100 Best Small Towns in America. Patricia Schultz called it the perfect American small town in 1,000 Places to See Before You Die. The list of accolades go on and on when it comes to Essex and for good reason. The town is picturesque in every respect. Ride the Essex Steam Train for a retro trip around the town. Visit the First Baptist Church of Essex, built in Egyptian Revival tradition. If possible, stay at The Griswold Inn. The building has stood for nearly 250 years and is one of the oldest operating inns in the country.


Boats on the dock in Mystic, Connecticut.
Boats in Mystic, Connecticut.

This pretty seaside town’s history, like many along the coast, is inextricably bound to the sea. Mystic's maritime tradition is palpable, and the sound of gulls cawing can be heard from almost anywhere within its limits. Visit the Mystic Seaport Museum to see this history brought to life in sharp relief. Seafaring continues to be an important part of the town today, and the boats floating in the harbor are not only for show. Charter a marine tour and see the town as it was meant to be seen. The Mystic Aquarium has seals, beluga whales, and penguins for animal lovers. Looking for a souvenir to commemorate the first of many visits to the town? Visit the Olde Mistick Village. This open-air shopping center is constructed in a delightful 18th-century style which is a big hit with tourists.


Book Barn downtown on Main Street, Niantic, Connecticut.
Book Barn downtown on Main Street, Niantic, Connecticut. Image credit Rachel Rose Boucher via Shutterstock

Located on the Long Island Sound, Niantic is the storybook seaside village one pictures in the mind’s eye. The Niantic Bay Boardwalk is a grand, arcing pathway which offers an amazing view of the water and a fishing jetty for anglers. Part of the greater town of East Lyme, Niantic is full of wonderful boutique vintage shops like Anna Pearl’s Curiosities, one of the premier antique shops in Connecticut. Visit Rocky Neck State Park for one of the best beaches around. Besides its soft sandy beaches, the park has picnic areas, spots for watching trains, and a multitude of trails for hikers for all skill levels. Rocky Neck is family friendly and a perfect place to spend an afternoon near the water.


An aerial view of the surrounding countryside from on top of haystack mountain in Norfolk Connecticut litchfield county.
An aerial view of the surrounding countryside from on top of Haystack Mountain in Norfolk, Connecticut.

A multiple-time winner of the "Best Small Town" award by Connecticut Magazine, Norfolk is an adorable small town to check out. Norfolk was established in 1758 and rests in the Berkshire highlands. Surrounded by the astounding Connecticut forests, Norfolk is a feast for the senses. Make a stop at the Infinity Music Hall and Bistro. Built in 1883 as a barbershop, saloon, and opera house, the establishment today is a place to enjoy live music and grab a bite to eat. History lovers will want to see the Beckley Furnace Industrial Monument, a 19th-century blast furnace that is on the US National Register of Historic Places. Next, the historical Berkshire Country Store serves classic food items and sports old-timey decor. Have a chicken melt 19th-century-style in Norfolk and let your taste buds travel back in time.


Fall colors and waterfront homes in Kent, Connecticut
Waterfront homes in Kent, Connecticut.

Complete with cozy inns, over a dozen waterfalls, and a plethora of hiking trails, calling Kent an adorable little town is an understatement. This Connecticut gem is only a short train ride from New York City, but the glass and steel skyline of the Big Apple quickly gives way to Appalachian wonder. Check out Bulls Bridge and the inn which shares its name. As far as accommodations go, Bulls Bridge is excellent, and the food served there is spectacular. Kent’s Eric Sloane Museum is a must-see destination for the artistically inclined, and the Connecticut Antique Machinery Association is the place to be for locomotive enthusiasts. Visit Kent Falls State Park to see its many trails and a series of waterfalls.


Villa Bella Vista, Chester, Connecticut, home covered in green vines.
Villa Bella Vista, Chester, Connecticut. Image credit JERRYE & ROY KLOTZ. M.D. via Wikimedia Commons

The town of Chester is something to behold; its quiet streets evoke memories of simpler times. Houses in Georgian and Post-Medieval English style are nearly everywhere, lending to the town’s old-world charm. The Beth Shalom Rodfe Zedek synagogue is a high point of Chester’s architecture. This town in the Connecticut River Valley is a local favorite, and it is easy to see why. Stroll down Main Street to find small businesses like Honeycone Craft Ice Cream set up inside historical 19th-century buildings. Gillette Castle State Park is nearby for touring, and accessible by ferry.


Tower Bell of Putnam, Connecticut with flowers at the base.
Tower Bell of Putnam, Connecticut.

Found in the state’s northeast, Putnam is a stunning town to behold. The town is pretty all year, but especially so in the fall when the many trees begin to change colors. The Quinebaug River, which borders the town, is a great place to swim in the summer, whereas the Putnam River Trail is enjoyable regardless of season. In town, walk the historic downtown district which has a thriving art community with galleries galore. The Bradley Theatre is well-respected and known to put on quality performances. The Gertrude Chandler Warner Boxcar Children’s Museum is a family-friendly attraction perfect for the little ones.


View from road one to Church Lane in beautiful spring day, Miro Vrlik Photography /
 Church Lane in beautiful spring day. Image credit Miro Vrlik Photography via

Beach lovers need look no further. Westport has three public beaches to its credit and plenty to do once the sun goes down. Located on Connecticut’s Gold Coast, scenic Westport is known for its bustling atmosphere, great food, and many beaches. Compo Beach, in particular, is one of the best in the state. The Levitt Pavilion often hosts free outdoor concerts in the summer. Walk along the Saugatuck River without leaving the town’s downtown area. Try a Sunset Kayak Tour or visit Sherwood Island State Park, Connecticut’s first state park. MOCA Westport is a contemporary art museum that more than holds its own when compared to those in nearby New York City.


First congregational church of Litchfield Connecticut.
First congregational church of Litchfield, Connecticut.

With a population of around 8,000 and gorgeous trees throughout, Litchfield is an ideal place to unwind and reset. Less than an hour’s drive east of Hartford, Litchfield is New England stock through and through. The local Historical Society and Litchfield Historic District are well-suited to experience the colonial architecture and for anyone on a blue-light detox looking to learn the old-fashioned way. Tour the white picket-fenced neighborhoods or head to Topsmead State Forest for a true getaway. The forest is a great picnic spot, and guided tours around the grounds are available. Be sure to drop by the Haight-Brown Winery, the state’s first, for a hot spiced wine by the fire, an especially delicious treat in the fall.


The red Hale barn, Colebrook
The Hale barn, Colebrook.

This unspoiled example of early 19th-century New England history is a marvel to behold. Northwest of Hartford, Colebrook drips with old-world charm. Rolling hills extend in nearly every direction, and the thickets of trees change colour magnificently in autumn. Swing by Gaylord Pond for a quick dip, and the Lake Triangle Dam has plenty of brook trout and rock bass. The Haystack Mountain Observation Tower offers a breathtaking view of both the Long Island Sound and the greater tri-state area. Colebrook is also known for its 4th of July celebrations, so prepare for the town to come alive in the summer.

Connecticut is bursting with amazing sights, sounds, and tastes. From the Gothic Revival architecture, which has been expertly preserved for continued appreciation, to the many lakes, rivers, and streams available for public use, there is always something to do or see in the Constitution State. Climb lighthouses and traverse the vast state parks the state has to offer. Connecticut’s adorable small towns are thriving and are ready to explore.

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