Downtown street in Stonington, Connecticut. Image credit Joe Tabacca via Shutterstock

8 Most Underrated Towns In Connecticut To Take A Trip To

Connecticut boasts many good reasons for tourists to want to explore it. As the fifth oldest state in the US (it ratified the US Constitution in 1788), Connecticut boasts a rich history, with many of its smaller, often-overlooked towns and villages having borne witness to important events that not only helped shape the state, but the US as a whole.

Add to this Connecticut’s natural beauty and cultural heritage, and you’ll find yourself having no end of fun, whatever your interests. Discover the eight most underrated towns in Connecticut to take a trip and learn more about some of the best places to visit in the Constitution State.


Tower Bell of Putnam, Connecticut.
Tower Bell of Putnam, Connecticut.

Located in a scenic area of northeastern Connecticut known as the state's Quiet Corner, Putnam’s lovely riverside setting makes it the ideal spot for a day trip or weekend getaway from larger, more popular places to visit, such as Boston or New York. Quinebaug River isn’t only picturesque, it’s also fun to play on, with activities such as canoeing and kayaking attracting both novice and experienced paddlers; it’s also the scene of an annual rubber duck race that adds to the town's quirky charm.

Other fun things to do in Putnam include shopping for collectibles and old treasures at the sprawling Antiques Marketplace, one of New England's largest antique malls with around 350 vendors. Explore its vibrant brew scene, a favorite being Bear Hands Brewing Company. Putnam is also home to a thriving art scene, with venues such as the Silver Circle Gallery exhibiting works by local artists.


A woman examines a display at the Connecticut Antique Machinery Association in Kent, Connecticut
Connecticut Antique Machinery Association in Kent, Connecticut. Image credit Marcelo Murillo via Shutterstock

Despite its population of only around 3,000 residents, the small Connecticut town of Kent boasts numerous good reasons for visitors to pay a visit. Its location close to the state border with New York and the fact it’s only 80 miles north of New York City make it an excellent choice for a day trip or overnight stay. A number of heritage buildings in the town have been transformed into boutique-style accommodations under the umbrella of the Kent Collection and offer a variety of unique historic places to stay.

You’ll also want to explore the surrounding Litchfield Hills region, which is even prettier when the fall colors arrive. Other highlights include Bull’s Bridge, a historic covered bridge; Kent Falls State Park, famous for its beautiful waterfall; and the Eric Sloane Museum, which showcases an impressive collection of early American tools and machinery.


Street view in Stonington, Connecticut.
Street view in Stonington, Connecticut, By Pi.1415926535 - Own work, CC BY-SA 3.0, File:Water Street at Church Street, Stonington, CT.JPG - Wikimedia Commons

The coastal community of Stonington has much to offer curious travelers in search of somewhere unique to explore. Established in 1658 and rich in history, include Stonington Point on your itinerary. In addition to the ocean views, it’s just a short stroll from the Stonington Lighthouse Museum, which has been a beacon for sailors since 1840. You will also learn more about the town at the interesting Captain Nathaniel B. Palmer House, built between 1852 and 1854 and named after the legendary mariner and shipbuilder.

Other fun things to do include wine tasting at Stonington Vineyards and Saltwater Farm Vineyard, as well as visiting Beer'd Brewing Company for a local brew.


Ridgefield, Connecticut, USA: Keeler Tavern Museum and History Center.
Ridgefield, Connecticut, Keeler Tavern Museum and History Center. Image credit Ritu Manoj Jethani via

Ridgefield was established in 1709 and is even closer to New York than Kent, the 90-minute drive making it an ideal day trip. You can learn a great deal about the town and its role in Connecticut’s past at the Keeler Tavern Museum and History Center, a historical building dating from 1713 that played a role in the Battle of Ridgefield, an important engagement during the American Revolutionary War that occurred in 1777.

Other Ridgefield attractions include Weir Farm National Historic Site, the only national park in the US devoted to Impressionist painting, and the town’s lovely old Main Street, home to Ballard Park and well-preserved old architecture.


The beautiful tower sits on the Talcott Mountain State Park in Simsbury, Connecticut, United States.
Talcott Mountain State Park in Simsbury, Connecticut. Image credit Andy_Leclerc via Shutterstock

Although often overlooked by visitors exploring nearby Hartford, just a 25-minute drive to the southeast, Simsbury certainly has enough points of interest for it to be included on your Connecticut travel itinerary. Highlights include the Old Drake Hill Flower Bridge, built in 1892 and now a popular pedestrian route over the Farmington River that’s lined with flowering plants; and Stratton Brook State Park, home to an attractive covered bridge and biking and hiking trails.

Also worth seeing is Talcott Mountain State Park, just three miles to the east of town. This 574-acre green space is where you’ll find the 165-foot tall Heublein Tower and museum with its fantastic views of the Hartford skyline.

East Hampton

Comstock Bridge, East Hampton, Connecticut.
Comstock Bridge, East Hampton, Connecticut.

Take the scenic route from New Haven to Hartford, and you’ll likely pass through the historic town of East Hampton. First settled in 1639 and formally established as a Connecticut town in 1767, a number of important battles of the American Revolutionary War occurred here, most notably the Battle of Hartford Heights.

Fun things to do in East Hampton include hiking (or biking) the Air Line South State Park Trail, a nearly 50-mile-long abandoned railway line with historic bridges and trestles, and visiting the picturesque Comstock Covered Bridge. In the fall and the lead-up to Halloween, be sure to pop into Pumpkintown, US,​ for a fun family time finding the perfect pumpkin.


Sunken Garden at Hill-Stead Museum is a Colonial Revival in Farmington, Connecticut.
Sunken Garden at Hill-Stead Museum is a Colonial Revival in Farmington, Connecticut.

Popular for leaf peepers when those spectacular autumn colors arrive, Farmington has managed to retain its authentic village feel. Settled by the English in 1640, this historic community is one of the oldest in Connecticut and features several cultural attractions worth visiting. The Hill-Stead Museum, an elegant Colonial Revival house built in 1901, is home to an impressive collection of French Impressionist masterpieces. Be sure to spend time exploring its stately grounds, too.

Constructed in 1720, Stanley-Whitman House is one of the oldest homes in the area and now serves as a museum with displays relating to local people and events. If you enjoy a pleasant hike, tackle the over 80-mile Farmington Canal Heritage, which connects the area to Massachusetts.


A tractor parade in Chester, Connecticut, during a winter festival.
A tractor parade in Chester, Connecticut. Image credit Joe Tabacca via

The town of Chester is a must-visit for patrons of the arts and creative types, with numerous art galleries and studios to explore. Set on the Connecticut River with its access to the Atlantic Ocean, it’s also a popular spot for boaters, with facilities like Hays Haven Marina offering a range of services. The river is also a magnet for kayakers and canoeists.

A fun Chester adventure involves taking a short ferry ride across the Connecticut River to check out the fascinating Gillette Castle State Park. Set overlooking the river, this mock medieval castle can be toured and features interesting displays about its owner, a former Hollywood actor famous for playing Sherlock Holmes in films of the 1930s.

Look beyond the usual tourist hotspots of Connecticut, and you’ll find no end of fascinating smaller communities to visit. From historic battles for America’s independence to mock Medieval castles built by Hollywood stars of old, uncover the eight most underrated towns in Connecticut.


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