10 Overlooked Towns In Connecticut Worth Visiting

Connecticut boasts an impressive wealth of small towns that make perfect stops during a New England road trip. However, some communities receive barely any attention from travelers, despite having a more than fair share of tourist attractions. Blending relaxed rural flair, traditional family values, a soothing sense of community, and an idyllic natural environment, these hidden gems bring out the genuine character and allure of the Nutmeg State. Fortunately, they are spread throughout the state, from the rolling mountains in the west to the serene coastline in the south, providing a worthwhile vacation destination wherever you end up.

Whether drawn to antique shops on quiet main streets, scenic hiking trails in the countryside, waterfront dining, or historic architecture, these overlooked towns in Connecticut deliver rich experiences without the crowds. Between the secluded setting of Kent and the low-key location of Stonington, these under-the-radar locales are absolutely worth a detour.

Granby

Just 24 mins from Hartford, Granby is an affluent community in north-central Connecticut that embraces its picturesque countryside atmosphere and a quintessential small-town feel. Its rich natural scenery compels visitors to venture into the open spaces for some alone time with nature at Enders State Forest. Spanning nearly 1,500 acres of woodlands, wetlands, and waterfalls, this charming sanctuary features scenic nature trails for hikers seeking to admire the vibrant fall foliage. A tour of Bushy Hill Orchard rewards newcomers with family-friendly experiences, offering a chance to pet gentle farm animals, sample savory farm-to-table dishes, and enjoy freshly crafted ciders at a privately run establishment.

Elsewhere, the Salmon Brook Historical Society displays several historical structures along with corresponding archives, providing a rich backstory of the town dating back to the 18th century. A short walk from the museum complex, you can stop by Salmon Brook Shops for cute antiques, ranging from jewelry, furniture, books, and rustic art.

Sherman

This secluded town, located near the New York border in western Connecticut, attracts few tourists despite offering a fair share of rewarding experiences. At the heart of the community is the Sherman Historic District, where you can find old buildings that provide evidence of Sherman's enduring heritage. Prominent among these is the Old Store, a 200-year-old mercantile shop where guests can look for adorable gift items and peruse informative historical displays. This is not too far from the century-old Sherman Players, which entertains the townspeople with excellent stage productions, including classic plays, musicals, and concerts.

The outdoor inclined head to Deer Pond Farm Sanctuary to be one with nature. This 850-acre park presents 15 miles of hiking trails, allowing guests to explore its gentle wilderness and encounter native wildlife. Finally, don't leave Sherman without indulging your sweet tooth at the American Pie Company, whose scrumptious treats range from cookies and cakes to pizzas and sandwiches.

Washington

Washington is a relaxed community in rural Litchfield County, renowned for its historic architecture, rugged countryside, and numerous outdoor opportunities. Founded in the 18th century, the town's historic district is distinguished by its elaborate, old-world buildings. Highlights in the area include the Gunn Historical Museum, a 1781 home turned museum, responsible for preserving and sharing Washington's storied history. Meanwhile, the Institute for American Indian Studies provides an immersive lesson on Native American history, inviting guests to browse 12,000 years of artifacts and a 16th-century settlement.

Tourists who appreciate green settings can embrace the serenity of Hollister House Garden while discovering a beautifully landscaped English garden. But if you are feeling adventurous, Hidden Valley Preserve offers a 727-acre wilderness with rugged trails through dense woodlands that are perfect for ardent hikers.

Thompson

Thompson is an isolated town located on the northeastern tip of Connecticut, which doesn't receive much fanfare. However, visitors praise it for its outdoor adventures and historical attractions. It is home to Quaddick State Park, where tourists can unwind in a rich natural sanctuary, punctuated by lush woodlands and the shimmering surface of the Quaddick Reservoir. Visiting families in Thompson often gravitate towards Fort Hill Farms Corn Maze for a fun experience, where they can roam through a beautiful labyrinth, pet farm animals, sample delicious ice cream, and explore a pumpkin patch.

Elsewhere, history buffs can get a unique perspective of 19th-century Thompson at the William Mason House. This magnificent Gothic Revival mansion boasts affluent furnishings and artifacts that reflect the lifestyle of the upper-middle class during the period. However, a deeper and broader view of the community's dynamic history awaits guests at the Thompson Historical Society.

Ridgefield

Forty-five minutes from Stamford, this beautiful borough at the base of the Berkshire Mountains charms newcomers with its scenic outdoor scenery and a vibrant arts community. It beckons nature enthusiasts to discover an undisturbed sanctuary at Seth Low Pierrepont State Park, which offers over 300 acres of wilderness with opportunities for fishing, hiking, camping, and wildlife viewing. Art is at the heart of the Ridgefield faithful, with townsfolk often meeting inside the Ridgefield Playhouse to support local talent during invigorating plays and musical performances in an intimate 500-seat venue.

Several historical markers provide a unique look into the early days of Ridgefield, including the Keeler Tavern Museum and History Center. Built in the early 1700s, this rustic dwelling interprets centuries of local history with interactive exhibits. Finally, guests can also meet the friendly locals while enjoying tasty craft beers at Nod Hill Brewery in a welcoming atmosphere.

Stonington

Stonington is easily one of the most underappreciated small towns in Connecticut, with many tourists choosing to vacation in its more famous neighbor, Mystic. Situated along Long Island Sound, this coastal escape spoils visitors with sandy beaches, such as DuBois Beach. This popular outdoor space offers a blend of serene atmosphere, shallow waters, and stunning ocean views, perfect for swimming, beachcombing, and surfing. The community's maritime heritage is showcased at the Stonington Lighthouse Museum, where visitors can explore a collection of artifacts and relics within a 1840s stone structure.

A respectable wine-making scene invites oenophiles to try out some of the region's award-winning wines, including Chardonnay at Stonington Vineyards. Lastly, history buffs can get a feel for Victorian-era Stonington at the Captain Nathaniel B. Palmer House Museum, a 14-room dwelling with elegant Greek Revival and Italianate architecture.

Berlin

Berlin is situated squarely in the state's geographic center, just 30 minutes from New Haven, and lures vacationers with its stunning natural scenery, golfing opportunities, and fascinating historical heritage. Golf lovers have multiple options to indulge in their hobby, with Timberlin Golf Course providing 18 championship holes on well-groomed greens and fairways. Berlin's rich history dates back to its founding in the 18th century, and this is extensively documented by the Berlin Historical Society, where visitors can examine a vast collection of photographs, archives, and related memorabilia.

Meanwhile, Picture Show in Berlin invites vacationers to a modern movie experience, allowing them to watch the latest film on multiple 3D screens and easily access concessions. For an outdoor escape, visitors can head to Lamentation Mountain State Park, whose 47-acre territory provides a recreational playground for climbers, hikers, nature photographers, and picnickers.

Kent

An outdoor lover's dream come true, this rugged town on Connecticut's western border provides unlimited adventures in the great outdoors. Kent is awash with natural spaces, and ardent outdoorsmen come to play in the expansive wilderness of Macedonia Brook State Park. Spanning over 2,300 acres, with 10 miles of scenic trails, isolated campsites, and stunning overlooks, this adorable sanctuary attracts hikers, campers, mountain climbers, and fishermen. Meanwhile, Kent Falls State Park is better suited for sightseers and photographers, thanks to the gorgeous Kent Falls, which tumbles 250 feet into the Housatonic River.

But there is a lot more to do in Kent beyond the outdoors, and beer lovers will relish the refreshing taste of craft brews at Kent Falls Brewing Company. Alternatively, guests can explore the evolution of machinery at the Connecticut Antique Machinery Museum, which features exhibits of steam locomotives, mining equipment, tractors, and other interactive relics.

Griswold

Griswold is an unassuming town in Connecticut, known as the "Quiet Corner," that offers a reprieve from the popular urban hubs. It is an excellent getaway for outdoor enthusiasts, providing them with a 550-acre playground at Hopeville Pond State Park. This lovely natural space supports various recreational activities, including camping, fishing, picnicking, boating, and hiking. However, you can opt for a more laid-back outdoor activity by playing golf at the 18-hole River Ridge Golf Course and savor the rolling landscapes as you walk down the manicured greens between holes.

Over 50 delicious flavors of ice-cold treats promise to curb your sweet cravings at Buttonwood Farm Ice Cream. This popular establishment delights guests with fresh, homemade ice creams made from milk from the farm's cows.

Westport

Westport's proximity to major urban hubs like Fairfield and Norwalk means most tourists overlook it for its neighbors, but the town doesn't disappoint those who put their faith in it. This is thanks to beautiful real estate along Long Island Sound, including Compo Beach. Tourists often gather on this sandy stretch to enjoy the water views, picnic on the smooth sands, and revel in the spectacular sunsets. The Westport Country Playhouse offers theater connoisseurs something to look forward to, thanks to its extensive lineup of engaging plays, staged inside a historic 1835 tannery.

Elsewhere, those interested in the region's heritage can visit the Westport Museum of History and Culture. An extensive library of archives, art, textiles, artifacts, and memorabilia highlights the story of Westport since its establishment in the 1800s.

From Washington's beautiful countryside to Westport's cozy shoreline, these often-overlooked towns in Connecticut breathe fresh life into your travel experience. Far from the bustling tourist hubs, they offer a chance to slow down, commune with nature, and appreciate the genuine charm of New England in the United States. Whether you're planning a weekend getaway or a scenic road trip, these hidden gems invite you to discover the quieter, slower, and more soulful side of the Constitution State.