6 Little-Known Towns In Connecticut
Connecticut, one of the oldest states in America, is home to many interesting small towns that often remain under the radar of travelers to this beautiful corner of New England. While the majority of visitors to the Constitution State make a beeline for popular destinations like Mystic or New Haven, these lesser-known gems offer equally compelling reasons to be included in your Connecticut travel itinerary. They not only provide an authentic glimpse into Connecticut's rich heritage, they also each present an opportunity to explore its quieter yet equally fascinating side. Whether you’re a history enthusiast, a nature lover, or simply a casual traveler looking for somewhere a little different to go, these six little-known towns In Connecticut are worth the journey.
Litchfield
Established in 1719, Litchfield is a historic town in northwestern Connecticut with a rich colonial past. This attractive town played a vital role in the Revolutionary War and later became a hub for the abolitionist movement. Among its historic landmarks, the Tapping Reeve House and Law School, built in 1773, was America’s first educational establishment dedicated to the study of law and is now a museum offering fascinating insights into early education. Another must-see is the Litchfield History Museum. Run by the Litchfield Historical Society, it features first-rate exhibits and displays going right back to the area’s first settlers in the early 1700s.
Enjoy nature? The nearby White Memorial Conservation Center covers more than 4,000 acres with hiking trails and educational programs to enjoy, while Bantam Lake, Connecticut’s largest natural lake, offers boating and fishing, all within a few minutes' drive. The Litchfield Hills Farm-Fresh Market features local produce and crafts most Saturdays, all just minutes from the Historic District with its many well-preserved 18th-century buildings.
Old Saybrook
One of Connecticut’s oldest towns, Old Saybrook, was founded in 1635 at the mouth of the Connecticut River. This charming coastal town holds historic significance as the site of the Saybrook Colony in 1635, which later merged into the Connecticut Colony in 1644. The Katharine Hepburn Cultural Arts Center, named after the Hollywood star (and the town’s most famous resident), is housed in a historic 1911 building and serves as a cultural hub with regular performances.
You’ll also want to explore Fort Saybrook Monument Park which commemorates the site of the original colony along with spectacular views at Saybrook Point. Harvey’s Beach is a great family swim spot for its shallow waters and is perfect for summer outings. Speaking of fun things to do in the warmer months, June sees the Celebrate Saybrook Street Party kick off summer with live music and food vendors taking over Main Street.
Wethersfield
Wethersfield is known as Connecticut’s “most ancient town” and can trace its founding all the way back to 1634. Just a few miles south of Hartford, if you go (and you should!), start your adventure in the Old Wethersfield Historic District with its more than 100 homes dating back to the 17th and 18th centuries. Highlights here include the Joseph Webb House, built in 1752 and where George Washington planned parts of his Revolutionary War strategy. The Wethersfield Historical Society operates several museums including the Keeney Memorial Cultural Center, set in a large and elegant red-brick Victorian home that’s chock-a-block full of displays and artifacts from the town’s early days.
You should also visit The Webb-Deane-Stevens Museum for its tours of three historic houses, each carefully restored to reflect different periods of American history. The town celebrates its farming roots d at the annual Cornfest in September, featuring local food, live music, crafts… and plenty of family fun. Outdoor enthusiast? Be sure to include a visit to Wethersfield Cove, with green spaces like Cove Park being good places to kayak and relax (take a picnic).
Chester
Located in the lower Connecticut River Valley, Chester was established in 1836 and became an important manufacturing hub during the Industrial Revolution. Its quaint downtown is a delight to explore on foot, especially on weekends when the town hosts its Chester Sunday Market with fresh produce, baked goods, and live music, all on Main Street.
Be sure to also check out the Chester-Hadlyme Ferry, which has been operational since 1769 and connects Chester to Hadlyme on the east side of the river. Though a short journey, it’s well worth it for the scenic views… and the bragging rights. Cedar Lake, a peaceful spot just outside the town center, is a great spot to visit when the urge for a swim or on-water activity such as paddleboarding strikes.
Woodstock
Known as Connecticut’s “Quiet Corner” for its tranquil rural setting, Woodstock was settled in 1686 and features a mix of colonial history and country charm. Highlights of this little-known town include Roseland Cottage. Also called the “Pink House,” this striking Gothic Revival-style home was built in 1846 and is now a National Historic Landmark that’s open for tours. Also worth seeing, the Woodstock Academy, founded in 1801, is one of the state’s oldest secondary schools, and its campus includes several historic structures.
You can get a feel for the town’s pastoral past at places like Woodstock Orchards and Bakery Barn where you can pick your own apples and shop for local products and sweet treats (try their famous HoneyCrisp!). The annual Woodstock Fair, held over Labor Day weekend since 1860, is one of the state’s largest such events and features agricultural exhibits, wagon rides, and live entertainment suitable for the whole family. For hikers and bikers, the nearby Air Line State Park Trail offers scenic routes through the surrounding woodlands.
East Haddam
Established in 1734 along the Connecticut River and less than an hour away from New Haven, East Haddam is home to several iconic landmarks that make it a worthwhile travel destination. The Goodspeed Opera House is a must-see. Built in 1876, it remains a premier venue for musical theater, while the Nathan Hale Schoolhouse, where the American Revolutionary hero once taught, offers a fascinating glimpse into the town’s colonial past. Gillette Castle State Park, located nearby, is another fun thing to do in Chester. This medieval-style mansion was built in 1914 by actor William Gillette, famous at the time for his portrayals of Sherlock Holmes.
The nearby Devil’s Hopyard State Park features hiking trails, a waterfall called Chapman Falls, and picnic spots. The best time to visit this part of Connecticut? Summer is always a great time for the opportunity to grab some memorable photos of the historic East Haddam Swing Bridge, built in 1913 and currently the subject of a major renovation project.
The Final Word
Connecticut’s lesser-known towns certainly provide a refreshing alternative to the state’s tourist-heavy destinations. Each of these towns offers distinct attractions, from historic homes and museums to scenic parks and fun community events, while their small size is also a bonus, making a visit a more intimate, much less crowded experience. Whether you’re planning to explore colonial landmarks, hike forested trails, or attend a fun cultural event, these six little-known towns in Connecticut prove that sometimes the less-traveled roads lead to the most memorable discoveries.
