Top 15 Charming Small Towns to Explore in Connecticut

Connecticut is the southernmost state in New England, in proximity to major urban centers such as New York City. Home to Yale University, this state successfully maintains a rich colonial heritage in its charming rural towns. Embark on a journey along the back roads to uncover the scenic beauty that Connecticut presents, showcasing its magnificent mountains, rolling hills, and stunning foliage.

This guide presents an opportunity to experience the enchanting small-town charm of New England by highlighting the 15 most remarkable small towns in Connecticut.

1. Chaplin, Connecticut

Chaplin, situated in Windham County, derives its name from one of its earliest settlers, Deacon Benjamin Chaplin. Its main thoroughfare, Chaplin Street, is recognized as a Historic Place on the National Register of Historic Places. This quaint town invites you to indulge in its picturesque library or explore the local trails on foot or horseback!

During your visit, take the opportunity to hike to Diana’s Pool, a beautiful natural attraction you are sure to appreciate. Alternatively, if you prefer comfort food, stop by Bach Dor Cafe, an ideal location to satisfy your craving for fried food. Unwind at Passport Inn & Suites and allow Chaplin to transport you to a simpler era.

2. Colebrook, Connecticut

Colebrook, located in Litchfield County, takes its name from Colebrook County in England. This quintessential small New England town presents the perfect retreat from the demands of modern life. Stroll through the charming streets, engage with locals, and visit Rock Hall, a Historic Place on the National Register.

The town is particularly vibrant during the 4th of July celebrations, which are not to be overlooked! Visit the Colebrook Store for delectable food that many refer to as “edible history”. Treat yourself to a weekend getaway at Rock Hall Luxe Lodging for a chance to unwind.

3. Columbia, Connecticut

This town, located in Tolland County, is named after the American ballad “Hail, Columbia”. Its Columbia Greene Historic District is recognized on the National Register of Historic Places, making it a worthwhile destination to explore. The historic stone buildings dating from the early 19th century surround a picturesque green that evokes a sense of nostalgia for centuries gone by.

Columbia is ideally located just off the highway and boasts beautiful nature trails and wooded areas for exploration. The town features an excellent train museum, which is best visited in the summer when non-residents can access summer activities, including kayaking. Savor a sweet treat at Motta’s Pastry & Bake Shop Inc. before continuing your journey.

4. Cornwall, Connecticut

Cornwall, situated in Litchfield County, is a charming locale that captivates visitors. The poet Mark Van Doren wrote about the “Hills of Little Cornwall,” capturing the serene natural beauty found in the surrounding countryside. An autumn visit is particularly recommended to witness the foliage in its full splendor!

Even if you’re hesitant to venture into the countryside around Cornwall, the town itself is worthy of exploration. A visit to the West Cornwall Bridge—a rare example of a covered bridge in the area—is essential. Its vibrant red wood creates a stunning contrast against the lush greenery, so bring your camera. Take a leisurely walk around town to admire the delightful buildings resembling gingerbread houses. Enjoy a coffee at Wandering Moose Cafe and stop by Berkshire Country Store before departing.

5. Cromwell, Connecticut

Cromwell, located in Middlesex County near the center of Connecticut, was named after a riverboat named in honor of Oliver Cromwell. This historic New England town features two distinct historic districts: Main Street Historic District and Middletown Upper Houses Historic District, alongside the Sage-Kirby House. A visit here offers a glimpse into authentic old-time New England towns.

Wear comfortable shoes and explore River Highlands State Park, where you can enjoy lush greenery and a peaceful view of the river. Alternatively, head to Cromwell Meadows Wildlife Management Area to explore the area further! Bird-watchers will delight in the diverse birdlife available. Following your explorations, enjoy a meal at Ambrosia and take some time to relax.

6. Essex, Connecticut

Essex, also located in Middlesex County, is distinguished by its historical significance—it was one of the few American towns targeted by a foreign nation. During the War of 1812, the British commandeered the town, resulting in considerable but non-fatal losses. Essex emerged from this adversity with resilience, ultimately serving as an inspiration for the fictional town of “Stars Hollow” in the beloved series, Gilmore Girls!

Plan a visit to Essex to experience a still operational steam train or stay at one of the oldest inns in the area, the Griswold Inn. Catch up on reading at the Essex Library Association, or treat yourself to a spa day at the Spa of Essex. Enjoy a drink at the Black Seal or a meal at Olive Oyl’s. Indulge in the rich tapestry of history here in Essex; it is sure to be a memorable experience!

7. Kent, Connecticut

Kent, nestled in Litchfield County, was established in 1737 and initially focused on iron production. The town is traversed by the Housatonic River and is home to the historic Bulls Bridge. Nearby, you can also find the Schaghticoke Reservation and a segment of the Appalachian Trail!

A visit to Kent is an opportunity to reconnect with nature—Macedonia Brook State Park is perfect for hiking, camping, or picnicking while offering views of the Catskill and Taconic Mountains. Alternatively, explore Kent Falls State Park, known for its cascading waterfalls where fishing for trout brought in from state hatcheries is allowed. Once back in town, discover antique shops and boutiques or dine at the Fife n’ Drum Restaurant to recharge.

8. Madison, Connecticut

Madison, located in New Haven County on the shores of Long Island Sound, was settled in 1641 and officially designated as a town in 1826, distinguishing it as a rival to Guilford from which it separated. Enjoy a serene beach getaway at Madison’s coastal locations.

Explore Hammonasset Beach State Park for a picnic, nap, or camping adventure. Fishing from the pier is also a possibility here. Alternatively, engage in recreational volleyball at Surf Club Beach or rent a sailboat. Indulge in a unique dining experience at RJ Julia Booksellers and treat yourself at Quiet Cove Massage Therapy. Consider a stay at Scranton Seahorse Inn and allow the sea breeze to revitalize you.

9. Monroe, Connecticut

Situated in Fairfield County, Monroe offers proximity to vibrant metropolitan areas like New York City while ensuring the tranquility of rural living. The town is named after James Monroe, the fifth president of the United States. Its colonial charm makes it an ideal retreat for urban dwellers seeking relaxation.

Bring your bicycle and explore the various trails designed for cycling enthusiasts. Alternatively, enjoy the local craft beer offerings at Veracious Brewing Company or revitalizing coffee at Last Drop Coffee Shop as you take in the scenic beauty of the area. Savor a meal at Carl Anthony’s Trattoria and relish the peaceful ambiance that distinguishes this charming town.

10. Mystic, Connecticut

Mystic is located in New London County and is distinctive in that it lacks an independent government status, as it is not recognized as a separate municipality. The name “Mystic” is believed to stem from the Native American term “missi-tuk,” referring to a large river, which is fitting given its historical significance as a colonial seaport.

As a town steeped in maritime history, visitors can explore the maritime museum that showcases preserved sailing vessels. Additionally, the Mystic Aquarium and Institute for Exploration offers encounters with beluga whales. Stroll through historic Downtown Mystic and indulge in fresh seafood at S & P Oyster Co. Don’t miss out on a slice of pizza at Mystic Pizza, famously linked to the film of the same name featuring Julia Roberts!

11. Niantic, Connecticut

Niantic, located on the Long Island Sound adjacent to Niantic Bay, serves as a beautiful seaside resort destination. Named after the Niantic People, a Native American tribe that inhabited Connecticut and Long Island prior to European settlement, Niantic is surrounded by natural beauty, making it a prime vacation spot.

During your stay, take in the opportunity to sail on the bay. Explore the mile-long beach at Rocky Neck State Park or venture out to some of the smaller islands just off the coast, such as Gardiners Island. With options for summer camping or hiking during the off-season, Niantic offers year-round activities. Browse the books at the Book Barn and enjoy the eclectic shops along Main Street. Consider an extended stay at the Inn at Harbor Hill Marina and relish in the soothing sounds of the ocean.

12. Old Saybrook, Connecticut

Old Saybrook, founded in 1635 at the Connecticut River’s mouth, is located in Middlesex County. The Fort here controlled the main trade route to the upper river valley, and the Collegiate School of Connecticut, later renamed Yale University, originated in Old Saybrook.

Consider enjoying a stay at Saybrook Point Inn & Spa, which provides an opportunity to appreciate the birthplace of Yale. Spend some time walking along Harvey’s Beach or play a round of golf at Fenwick Golf Club. Visit the Lynde Point Lighthouse or explore antique shops at Long Ago Antiques. Indulge in a meal at Liv’s Oyster Bar & Restaurant and afterward, enjoy a relaxing drink at Fresh Salt.

13. Putnam, Connecticut

Putnam, located in Windham County, is named after Revolutionary War General Israel Putnam. The town developed around the textile mill industry and played a pivotal role in producing uniforms for Civil War soldiers. Visitors are encouraged to discover this charming New England mill town.

Attend a performance at the Bradley Playhouse or hunt for antiques at Jeremiah’s. Explore your creative side at Artique – a Paint Bar, or look at unique instruments at String Tinkers. Relax at the upscale Whitehaven Inn and enjoy a leisurely meal at 85 Main. Don’t forget to save room for dessert at Victoria Station Cafe!

14. Washington, Connecticut

Washington, a rural town in Litchfield County, is recognized for its proximity to New York City and its picturesque countryside, historic architecture, and vibrant cultural scene. Nestled in the foothills of the Berkshire Mountains, many residents can trace their lineage back to the Colonial era.

Wear your walking shoes for a visit to the Shepaug River that winds through Hidden Valley Preserve. Alternatively, see Lake Waramaug, Connecticut’s second-largest natural lake—make sure to capture its breathtaking scenery. While in town, visit Hickory Stick Bookshop or Hollister House Garden. Savor comfort at the Orange Gild Bed and Breakfast and treat yourself to an exquisite dining experience at the Mayflower Dining Room.

15. New Milford, Connecticut

New Milford, located in Litchfield County along the Housatonic River, was once inhabited by the Weantinock Native Americans, a faction of the Paugusset tribe, who farmed and fished here before John Noble established a community in 1707. The town played a role in the American Revolution by sending the 7th Connecticut Regiment to participate in notable battles such as the Battle of Brandywine.

New Milford invites you to visit Lovers Leap State Park or Harrybrooke State Park, ideal for serene picnics or invigorating hikes. Explore your culinary interests with a cooking class at the Silo Cooking School or discover the arts at the Village Center for the Arts. Savor sushi at Yokohama or decompress at the Homestead Inn. Here, tranquility awaits!