The Most Underrated Towns In Connecticut

Connecticut’s relatively small size, lack of a major international airport, and proximity to world-class cities cause many travelers to overlook it. Unfortunately, this is a fate shared by many of its small towns, despite their obvious potential to deliver an unforgettable holiday experience. This is the perfect reason to explore more of the Constitution State and learn about its rich culture, discover its stunning outdoor scenery, and delve into its captivating history. Fortunately, Connecticut is home to a handful of exquisite communities that personify the true character of the state.

These reward vacationers with remarkable experiences, from strolling the artist-filled streets of Ridgefield to basking in the pastoral serenity of Kent and its cascading waterfalls. Whatever floats your boat, here is the 2025 list of the most underrated towns in Connecticut, offering a tapestry of New England charm, creativity, and timeless beauty in the United States.

Westport

Despite being overlooked for other East Coast summer destinations, Westport is ranked among the best beach towns in Connecticut. This waterfront community enchants visitors with its silky smooth Long Island Sound beaches, such as Compo Beach. Spanning approximately 29 acres, the serene space offers opportunities for picnicking, swimming, and surfing against a stunning ocean backdrop. Sea Kayak Connecticut offers fun opportunities to explore the open water through paddleboard, kayak, and canoe rentals, accompanied by guided tours that showcase the stunning shoreline.

Westport's rich heritage is preserved at the Westport Museum for History and Culture, which safeguards an extensive collection of archives, art, antiques, and artifacts from the community, accumulated over the decades. Elsewhere, its artistic personality is evident at the Westport Country Playhouse, where residents gather to watch theatrical productions inside a repurposed Victorian tannery.

Groton

Nicknamed the "Submarine Capital of the World," Groton blends maritime heritage, history, and waterside beauty to deliver a fun experience for newcomers. The town sits on the banks of the Thames River and has a lasting connection to the U.S. Navy, evidenced by the presence of the Submarine Force Library and Museum. Thousands of photographs, artifacts, and documents chronicle a captivating story, with the highlight being the USS Nautilus. Bluff Point State Park attracts outdoor enthusiasts with its diverse range of recreational opportunities, including beaches, a sandy shoreline, wooded trails, and wildlife habitats.

This also applies to Esker Point Beach, whose 600-foot waterfront is a playground for swimmers, picnickers, and strollers. While in town, consider tasting refreshing handcrafted brews in a welcoming atmosphere at Outer Light Brewing Company.

New Canaan

New Canaan is an artistic community in Fairfield County, renowned for its close ties, art attractions, and beautiful natural areas. Every Saturday, downtown transforms into a vibrant gathering spot for local farmers, bakers, crafters, and vendors selling a diverse range of merchandise. The New Canaan Farmers Market brings new life to the corridor, offering a festive setting. The Carriage Barn Arts Center promotes the arts by staging exhibitions, performances, and community events to foster a culture of the arts.

Meanwhile, you won't want to miss the unique Glass House, a signature architectural gem by Philip Johnson, renowned for its transparent design. Those who love outdoor activities can opt to hike, stroll, or picnic in the cozy location of Irwin Park.

Ridgefield

This quaint borough in Fairfield County is one of the underrated towns in Connecticut, largely due to its isolated location near the New York State line, set near the stunning Berkshire Mountains. Ridgefield is an ideal getaway for outdoor adventurers, offering excellent opportunities for adventure at Seth Low Pierrepont State Park. This spans 305 acres of rugged trails through dense woodlands, designed for solo hiking excursions. It also gives culture vultures something intriguing to anticipate with access to the Ridgefield Playhouse. Housing an audience of about 500, the entertainment venue showcases movies, theater, and live performances. Guests can satisfy their curiosity about Ridgefield's history at the Keeler Tavern Museum and History Center. This 1700s mansion offers a rare glimpse into colonial life through diverse exhibits and programs.

Thompson

Thompson is a hidden gem in northeast Connecticut, delivering a fun blend of attractions that cater to both indoor and outdoor enthusiasts. It offers numerous options for seasoned outdoorsmen, providing access to a serene waterside playground at Quaddick State Park. This pleasant space is situated along the shores of the Quaddick Reservoir, offering opportunities for fishing, boating, and kayaking. A tour of the William Mason House transports guests into Victorian Thompson, an opulent Gothic Revival home that depicts the life of a wealthy resident during that era.

Additionally, the Thompson Historical Society delves deeper into local history with exhibits that cover all aspects of the community's past. Finally, be sure to watch a speed spectacle at the Thompson Speedway Motorsports Park, which hosts adrenaline-filled races to the public's amusement.

Branford

Branford is an often-overlooked escape on the Long Island Sound shoreline, presenting vacationers with the ideal blend of untouched natural beauty, relaxing vibes, and cultural experiences. Very near New Haven, the town is surrounded by a vast body of water that welcomes cruises to explore the area along the shore, courtesy of Thimble Islands Cruise. This mellow-paced sail takes visitors to the nearby Thimble Islands, an isolated region teeming with raw beauty. Alternatively, you can board a vintage trolley for an exquisite tour at the Shore Line Trolley Museum for a vintage ride.

Those who want to commune with nature are welcome to fish, hike, camp, and watch the wildlife that call Branford Supply Pond Park home, while theater enthusiasts can anticipate catching invigorating performances on stage by talented actors at the landmark Legacy Theatre.

Kent

Kent lures tourists with a penchant for uncrowded outdoor adventures, thanks to its secluded location near the western Connecticut border and rugged natural surroundings, punctuated by dense forests and undulating Berkshire Mountains. Visitors can expect complete immersion into wilderness adventures at the 2,300-acre Macedonia Brook State Park. This is a popular escape among campers, hikers, fishermen, and picnickers. Furthermore, Kent Falls State Park keeps the adventures going in one of the most beautiful natural backdrops in rural Connecticut.

It features the stunning Kent Falls, a 70-foot cascade that tumbles into the Housatonic River. But there is more to the town than adventure. After a long day lost in the wilderness, you can head back downtown and enjoy a relaxing pint of craft beer at Kent Falls Brewing Company.

Stonington

Stonington is often overshadowed by its more famous neighbor, Mystic, but it doesn't disappoint those who take a chance on it. This lovely coastal town provides access to a sandy shoreline at DuBois Beach, serving as a recreational hub for swimming, picnicking, crabbing, surfing, and other enjoyable activities. From the beach, you can spot the towering Stonington Lighthouse, which dates back to the 1840s and features a museum with exhibits that document over three centuries of regional maritime heritage.

Stonington boasts a respectable wine-making culture, with vineyards and wineries scattered across the town. If you appreciate the taste of finely crafted wines, consider touring Stonington Vineyards and sampling its premier European-style wines.

Hidden Gems In Connecticut

Whether craving a chilled-out escape to the beach in Westport or an adrenaline-filled adventure through the wilderness of Kent, these most underrated towns in Connecticut make you appreciate the pleasures of the countryside. Their quiet roads, hidden waterfalls, and peaceful shores remind seasoned travelers what it means to truly slow down. Away from the bustle of big cities, they offer serenity, authenticity, and a rare chance to reconnect with nature, history, and down-to-earth locals.