6 Most Overlooked Towns in Connecticut
Connecticut, a New England state and one of the original thirteen colonies, boasts a heritage steeped in both Puritan and Native American history. It is affectionately known by its nicknames, most notably the Constitution State and the Nutmeg State. Today, it is celebrated for its striking coastal shores and rural landscapes, featuring farmlands and rolling hills. While well-loved towns like Hartford and Greenwich enjoy popularity, numerous overlooked towns offer just as much charm and appeal. Here are six underrated Connecticut towns that travelers should consider visiting, whether in search of a lively evening or a tranquil retreat.
Stonington
Stonington, unique for being the only Connecticut town with Atlantic Ocean frontage, offers a coastal escape often overshadowed by more famous destinations like Groton or Mystic. Situated in New London County, near these tourist hubs, Stonington presents a more rural atmosphere with its sprawling farmlands and iconic stone walls. As the state's oldest borough, established in 1801, Stonington contributes significantly to the area's rich cultural history. Despite its small-town tranquility, Stonington is less than a 30-minute drive from Connecticut's premier casinos, Foxwoods and Mohegan Sun, which boast some of the finest dining, entertainment, resort lodging, and shopping options in New England.
Visitors interested in the town's maritime heritage should not miss the Stonington Lighthouse Museum. The lighthouse, operational from 1840 to 1889 and now maintained by the Stonington Historical Society, displays a wealth of historic artifacts and offers an ascent of 29 steps to its summit. Additionally, the town is home to two esteemed vineyards, Saltwater Farm Vineyard and Stonington Vineyards, each featuring tasting rooms to sample local wines and spaces for private events.
Thompson
In the 'quiet corner' of Connecticut lies Thompson, a northeastern town that straddles the borders of Massachusetts and Rhode Island. Highlighted by the Tri-State Marker Trail, visitors can embark on a roughly 2-mile hike to a century-old stone marker and stand in three states simultaneously. Thompson, part of Windham County and comprising ten distinct villages, boasts a population just under 10,000. Among its hidden treasures is Quaddick State Park, a park and recreational area on Middle Quaddick Reservoir's shores, offering a sandy beach, a designated swimming zone, and picnic spots.
Thompson also prides itself on the Thompson Speedway Motorsports Park, a landmark since its opening in 1940 and a hub for NASCAR-sanctioned races in New England. A visit to Fort Hill Farms during autumn's peak foliage reveals an array of family-oriented activities, from pumpkin picking and exploring an exquisite garden to navigating a corn maze, which even offers nighttime adventures under the stars. Thompson stands out as a truly underrated gem, brimming with attractions across its picturesque rural setting.
Torrington
Torrington, located in Litchfield County along the Naugatuck River, is the largest town in the county. Despite its size, it maintains a low-key atmosphere, free from the hustle and bustle of standard tourist attractions. Originally known by names such as Mast Swamp and New Orleans Village, the town was renamed Torrington in 1881, taking inspiration from Great Torrington, England. Torrington holds historical significance as the birthplace of John Brown, a notable figure in the Underground Railroad, with his childhood home being a prominent site on the Connecticut Freedom Trail. Visitors can explore John Brown's birthplace on John Brown Road, where a trail meanders through captivating natural surroundings.
A visit to Torrington offers numerous opportunities to immerse oneself in nature and enjoy the town's serene landscape. Burr Pond State Park, covering over 400 acres adjacent to Paugnut State Forest, features swimming, fishing, boating, and picnic areas suitable for families. Sunnybrook State Park caters to hiking enthusiasts, offering trails accessible to all skill levels and designated exclusively for foot travel. Additionally, for those visiting in the fall, The Forsaken Lands Outdoor Haunted Attraction, a short drive from Torrington, ranks as one of Connecticut's most thrilling Halloween destinations.
Old Saybrook
Old Saybrook, nestled at the confluence of the Connecticut River and Long Island Sound, combines historical allure with coastal charm. This unique geographical positioning affords visitors a mix of sandy beaches, dense forests, and a quaint downtown area brimming with locally owned shops and eateries. A visit to Fort Saybrook Monument Park, covering 17 acres, allows guests to delve into the town's rich history, with storyboards illustrating life in the Saybrook Colony during the 1600s.
For antique enthusiasts, the Essex Saybrook Antiques Village offers an unparalleled shopping experience. Open on both weekdays and weekends, this village features over 50 booths selling a diverse array of historical artifacts, collectibles, and furniture. Harvey's Beach is a beloved public beach in Old Saybrook, renowned for its fishing and boating areas, as well as the presence of lifeguards during the open season. To cap off a day of exploration, Penny Lane Pub in the historic district serves up English-style pub fare and beverages, providing a cozy retreat for visitors and locals alike.
Cheshire
Cheshire is a town in Connecticut with a population of roughly 30,000 people. It is celebrated as both a prime vacation destination and a fantastic place to live, having garnered recognition as one of the best places to reside in the state. Presently, Cheshire is recognized as a flourishing agricultural community in New Haven County, although it retains much of its historical charm from its days as a former mill village. The town's suburban atmosphere makes it ideal for families looking to settle down or for individuals seeking a serene retreat conveniently situated between Hartford and New Haven. Visitors in early June should not miss the Strawberry Festival and Craft Fair, a cherished town tradition featuring live performances, children's rides, and delectable strawberry shortcakes.
To enjoy Connecticut’s splendid spring and summer weather, a visit to Roaring Brook Park in Cheshire is highly recommended. This public park offers nearly 2 acres of well-maintained land and boasts some of the town’s finest hiking trails. Drazen Orchards is another notable attraction, open from July through Thanksgiving weekend, where visitors can enjoy locally grown vegetables, farm-fresh honey, and hot apple cider donuts on weekends. A unique destination in Cheshire is the Barker Character Comic and Cartoon Museum on Highland Ave, housing over 80,000 vintage items that showcase iconic toys and media from various decades.
Pomfret
Pomfret, established in 1713, ranks among Connecticut’s oldest small towns. This rural locale is renowned for its picturesque rolling hills, particularly along the scenic Route 169 adorned with historic homes from the 18th and 19th centuries. Pomfret is also home to the Connecticut Audubon Society Center, which offers an educational center and opportunities for bird-watching and wildlife observation. Another significant site is the Israel Putnam Wolf Den, listed on the National Register of Historic Places, where Connecticut's last wolf was reportedly killed.
Visitors can explore the Wolf Den by visiting Mashamoquet Brook State Park, the premier destination for outdoor activities in Pomfret. This state park spans over 1,000 acres, including Mashamoquet Brook, the Wolf Den, and the area known as Saptree Run. It is open year-round for hiking, boating, fishing, and biking. After a day outdoors, The Vanilla Bean Café on Deerfield Road offers excellent coffee, classic dishes, and occasional live entertainment, providing a perfect end to the day.
While Connecticut is quintessentially New England in spirit, it stands out with its unique charm and character. Beyond the more recognized cities like Hartford and Stamford, the state is dotted with small towns that boast unique attractions not found elsewhere. From the serene hills of its quiet corners to the coastal beauty of Stonington, Connecticut’s small towns offer rich experiences for travelers eager to discover new places or for those considering a move to the Constitution State.
