View of Westport, Connecticut, from Downtown Bridge overlooking the town and its reflection in the river.

9 Must-Visit Small Towns in Connecticut

Is a New England adventure in your future travel plans? Connecticut fits the bill. Halfway between Boston and New York City and most other northeast cities, this compact state is home to a vast array of small towns perfect for a weekend getaway or day trip. Travel back in time and experience a well-preserved rich history dating back to the Native Americans and earliest European settlers. Take part in a myriad of outdoor activities year-round. Be a high roller at a world-class casino, and with your winnings, fingers crossed, splurge at the designer outlets. Connecticut’s small towns offer something for everyone.


Joseph Webb and Isaac Stevens Houses in Wethersfield, Connecticut, USA. Built in 1781 and 1789, respectively.

Joseph Webb and Isaac Stevens Houses in Wethersfield, Connecticut, USA. Built in 1781 and 1789, respectively.

With over 375 years of history, heritage tourism takes center stage in Wethersfield. Committed to maintaining its rich community identity, its residents proudly let anyone know that their home was the first town settled in 1634.  Any first-time visitor should start their adventure at the Wethersfield Historical Society. Join one of their walking tours and learn about the Wethersfield witch trials, which predated the Salem witch trials. Then, explore its ancient burying grounds and cemetery. Interested in learning what it was like to live during the 18th and 19th centuries? The Webb-Deane-Stevens Museum offers an authentic, living New England village. Head to The Old Wethersfield Historic District and explore over 150 structures built before 1850. After walking in the steps of history, relax in your luxurious accommodations at the Chester Bulkley House Bed & Breakfast. For a farm-to-table food experience, the Heirloom Market at the Comstock-Ferre will satisfy your taste buds. 


Exterior of Book Barn Downtown edition on Main Street in Niantic, Connecticut, USA, after a recent rainfall.
Exterior of Book Barn Downtown edition on Main Street in Niantic, Connecticut, USA, after a recent rainfall. Editorial credit: Rachel Rose Boucher /

Looking for a perfect seaside village experience? Niantic, on the Long Island Sound, paints the ideal picture. Stroll along the mile-long Niantic Bay Boardwalk, with stunning views of Niantic Bay and bookended by beaches. Enjoy one of the many fishing adventures Striper Snax offers or the Black Hawk offers. Prefer not to test your sea legs? Pack a picnic and enjoy the views. Head to Rocky Neck State Park, where clear waters and white sand make it ideal for swimming. Diverse trails provide easy and enjoyable walks to the scenic salt marsh and points of interest such as Baker's Cave, Tony's Nose, and Shipyard. Traveling with kids or just a kid at heart? Check out the Children’s Museum of Southeastern Connecticut, where interactive fun takes center stage at their 5,000-square-foot facility. Stroll along Niantic's Main Street and visit its many eclectic shops, including The Book Barn, a bookstore boasting over 350,000 titles, including rare and out-of-print books.


Antique train at Essex Train Station in Essex, Connecticut.

Antique train at Essex Train Station in Essex, Connecticut.

Dubbed “The Perfect Small American Town” by the travel guide 1,000 Places to See Before You Die, Essex offers tree-lined streets perfect for leisurely walks and are a colonial architecture lovers delight. Take in the area’s scenery on an hour-long ride through the Connecticut wilderness on the Essex Steam Train. Fall is a beautiful time of year to partake in this adventure. Combine your steam-train adventure with a riverboat adventure for double the fun. Sitting at the mouth of the Connecticut River, known as the longest river in New England, a visit to the Connecticut River Museum is a must. Are you an adrenaline junkie? Drive about an hour north and experience the fall colors by zip line at The Adventure Park at Storrs. Book a stay at the Historic Griswold Inn, the oldest continuously operating inn in the country. Whether or not you stay over, dine at their rustic tavern and top off your day with ice cream at Sweet P’s Ice Cream and Organic Juice Bar. 


St. John the Evangelist Catholic Church in Uncasville, Connecticut.
St. John the Evangelist Catholic Church in Uncasville, Connecticut. Editorial Credit: By Farragutful - Own work, CC BY-SA 4.0,

Are you feeling lucky? Uncasville is home to Mohegan Sun Casino Resort, a premier entertainment destination, which includes a  casino, restaurants, entertainment, nightlife, shopping, and much more—looking for even more high-stakes and slot machines? Head down the road to the Foxwoods Resort & Casino in Mashantucket. Need a break from the action and glitz?  Steeped in Native American history, history buffs can explore the Tantaquidgeon Indian Museum, the oldest operating Indian museum in America, and immerse themselves in Mohegan culture. Step back at the Fort Shantel Archeological District, the Mohegan Tribe’s main settlement from 1636 to 1682, featuring preserved Native American and sacred ground. To go further back in time when dinosaurs roamed the earth, families can explore The Dinosaur Place at Nature’s Art Village, home to over 50 life-size dinosaur replicas. 


Historic stone 1639 Rev. Henry Whitfield House and Museum in Guilford, Connecticut.
Historic stone 1639 Rev. Henry Whitfield House and Museum in Guilford, Connecticut. Editorial credit: LEE SNIDER PHOTO IMAGES /

Blessed with the best of what nature offers, the coastal town of Guilford offers miles of seashore, lakes, rivers, and forests. It is also home to one of New England's most significant collections of preserved historic homes. Take your pick in touring several living history museums, including the Henry Whitfield House, which dates back to 1639 and is both Connecticut's oldest existing historic home and the oldest preserved stone house in New England. Learn how farmers worked the land pre-industrial revolution at the 300-year-old Dudley Farm Museum. Hikers can lace up and get walking at the gateway of the New England National Scenic Trail. Head over to Bishop’s Orchards, a family farm and winery, to pick fruit, taste their wines, or buy groceries at their farm market. Lobster, anyone? Top off your day with some of the best seafood. In warmer months, The Place Restaurant offers outdoor tables and an 18-foot fire pit for visitors to dine around. The Guilford Lobster Pound sells fresh-caught lobster daily. Off-season, when there is a chill in the air, there are plenty of other choices to dine indoors. 


The Hale barn in Colebrook, Connecticut, USA, showcasing typical 18th-century barn construction.

The Hale barn in Colebrook, Connecticut, USA, showcases typical 18th-century barn construction. 

Is relaxation on your travel menu? The sleepy town of Colebrook, nestled in the Connecticut countryside, delivers. North of Hartford's hilly location makes it particularly stunning in the fall. Spend an afternoon at Norbrook Farm Brewery. Sample some beers, enjoy food trucks, hike its trails, and make friends with farm animals. Head over to the 2,500-acre Algonquin State Forest, a managed wildlife habitat. Its top recreational activities include hiking, hunting, fishing, and bird watching. Looking to cast a line? The 700-acre Colebrook River Lake is perfect for a day of fishing or relaxing by the water. Interested in panoramic views of the Long Island Sound and the tri-state area? Drive just 15 minutes to the 34-foot Haystack Mountain Observation Tower, where you can view the Berkshires and peaks in Massachusetts, New York, and the Green Mountains of Vermont. Be warned. You can only drive halfway up to the top. You must lace up your hiking shoes and take a rugged half-mile trail to reach the summit. But it will be worth it!


Covered bridge along scenic Route 7 in West Cornwall, Connecticut, USA.

Covered bridge along scenic Route 7 in West Cornwall, Connecticut, USA.

Located on the Housatonic River, Cornwall may be small, but its stunning New England scenery, especially in Fall, more than makes up for its size. Dubbed the greenest town in Connecticut, this quiet town is a town for all seasons. Visitors to Mohawk State Forest enjoy activities such as river rafting, canoeing, and fly fishing. Take a hike through the rugged hills of this wildlife sanctuary. In winter, head to Mohawk Mountain Ski Area, the largest in Connecticut, with 25 trails and seven lifts on 330 acres of land. Home to one of the few covered bridges in the state, the 1762 West Cornwall Covered Bridge is still in service and is a photographer's dream. The town’s gingerbread house buildings look like they just stepped out of a holiday movie. After a full day of outdoor fun and fresh air, unwind in your room at The Cornwall Inn, a historic hotel that dates back to the 1800s. 


Lake Garda School in Burlington, Connecticut.

Lake Garda School in Burlington, Connecticut. By John Phelan - Own work, CC BY-SA 4.0,

Burlington is the perfect place to spend time with family and loved ones and reconnect with each other and nature. Nestled in the foothills of the Berkshires, atop Johnnycake Mountain, wide open spaces and natural charm are what rule here. Head over to nearby Nassahegan State Forest and take your pick of 30 miles of Blue-blazed hiking trails, ride a mountain bike trail, or fish, kayak, or canoe on the Farmington River. Visit the Burlington State Fish Hatchery, where 100,000 pounds of trout and salmon are raised to stock state waters. Do you love pancakes and waffles? Check out Lamothe's Sugar House and watch how maple syrup is made.  Pick up fresh vegetables at a nearby farm stand. Relax afterward with coffee and a scone at Renaissance Farms. Enjoy the town green, where the town’s one-room schoolhouse sits nearby, and visit the Elton Tavern, listed on the National Register of Historic Places and just a few steps away. Make sure to have a meal at the Greenhouse Cafe & Tavern or Sabrina's Restaurant.


View from Westport bridge over Saugatuck River and architecture near downtown in Westport, Connecticut, USA.
View from Westport bridge over Saugatuck River and architecture near downtown in Westport, Connecticut, USA. Editorial credit: Miro Vrlik Photography /

Just 50 miles outside New York City, Westport sits on Connecticut's Gold Coast, prime real estate along the Saugatuck River. With its world-class shopping, big designer names, and top-notch restaurants, its main street still maintains its quaint and small-town feel. In the summer, concerts fill the air at The Levitt Pavilion. Explore MOCA Westport, a contemporary art museum that can rival any big city museum. Book tickets to a play at the Westport Country Playhouse, where many big-name stars have graced the stage. Watersports enthusiasts can indulge at Compo Beach, Old Mill Beach, and Sherwood Island. Is collecting antiques a passion? Westport and the surrounding area are part of the Connecticut Antiques Trail. End your day with a stroll on the riverwalk to watch the sunset. 

Embark on a Memorable Connecticut Journey

For an authentic New England experience, put Connecticut on your list of places to explore. Dotted with a vast array of charming small towns, this state offers the perfect balance of rich history, outdoor adventure, entertainment, and delicious cuisine. Choosing which village to visit first will be your most challenging task. So what are you waiting for?

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