Connecticut's 9 Most Underrated Towns to Visit in 2024

The state of Connecticut has a long history. First home to a variety of Native American people groups such as Pequots, Mohegans, and others, Europeans first began to settle the area in the 1600s. In 1639, the colony wrote up the Fundamental Orders, a constitution that earned the state the nickname "The Constitution State."

In 1788, Connecticut officially ratified the Constitution of the US, becoming the fifth state. Today, the small state of Connecticut is a beautiful place with many small communities, destinations, and historical locations, which you can visit today if you are willing to explore a few overlooked towns.

Don't pass up on these nine underrated small towns in Connecticut in 2024.

Stonington

First settled in 1752, this village between New York and Boston has a number of great spots to check out for boating lovers. Most notable is the Stonington Lighthouse Museum. First built in 1840, this historic lighthouse with its ornamental cornices is the pride of the town. Dip your feet in the water at Dubois Beach or go for a walk at one of the villages' many preserves, such as Fennerswood Preserve, Hoffman Evergreen Preserve, or the Knox Family Farm. Relax at the end of the day with a glass of wine from the Saltwater Farm Vineyard. When it comes to vibrant Connecticut towns, this one definitely stands out.

Pomfret

With more than 4,200 residents, Pomfret offers quaint surroundings with beautiful country roads and charm. Founded in 1713, it was one of the oldest communities in the entire state. It provides many places for walking, mountain biking, and more, such as the Mashamoquet State Park, Wolf Den, and Air Line Trail. For bird watchers, the Connecticut Audubon Center at Pomfret is a great spot. Learn about the history of blacksmithing in the town at the Brayton Grist Mill & Marcy Blacksmith Museum. Don't forget to try out some of the local eateries, such as The Vanilla Bean Cafe and Pizza 101.

Chester

With just shy of 4,000 residents, Chester is a fun town with hidden treasures that one wouldn't expect to find in New England. The town's pride and joy is the Chakana Sky Alpacas farm. Visitors can come pet these fuzzy alpacas free of charge. Visitors can take a relaxing ride across the Connecticut River on the Selden III ferry. Learn about how early settlers lived at the Chester Museum at the Mill, which features a scenic waterfall. Before you leave town, visit the Chester Meeting House, a historic building that has been in operation since the 1840s. This friendly Connecticut town also offers a self-guided walking tour called Chasing Squirrels, which you can find on their website.

East Haddam

Located on the shores of the Connecticut River, East Haddam is a place of great artistic and natural beauty. With just shy of 9,000 residents, the town is close to a New England Treasure, Gillette Castle State Park. The park contains a 14,000-foot castle built by actor William Hooker Gillette in 1914. The community has plenty of other forests and gardens to explore as well, such as Salmon River State Forest and Devil's Hopyard State Park, which contains the scenic 60-foot waterfall Chapman Falls. After a day of exploring, enjoy a musical at the Goodspeed Opera House.

Essex

Essex is a fun town filled with fascinating historical places to visit. Although it didn't become an official town until 1852, its history stretches back to the 1700s, as it built the first battleship in Connecticut in 1774: the Oliver Cromwell. Today, just over 6,600 people call this town home, which hosts the fascinating Griswold Inn, one of America's oldest taverns, which famously defied Prohibition by continuing to serve alcohol. Essex is also home to the Essex Steam Train and the Connecticut River Museum, which houses the Turtle submarine used during the American War of Independence. For other activities, consider visiting the Essex Indoor Golf Center or try out some delicious treats at Chocolate Geeks.

Old Saybrook

The town of Old Saybrook earns its name as it was settled in 1635 on the spot where the Connecticut River meets Long Island Sound. Today, just over 10,000 people live in the town, but it is far from a sleepy place. It is home to the Katharine Hepburn Cultural Arts Center and Museum, which brings in international acts with its 285-seat theater. There are plenty of boating companies that offer fishing, such as Eden Charters and Kingfisher. Saybrook Point Park offers season minigolf and great views of the Connecticut River. For hikers, consider The Preserve, a 963-acre forest, one of the largest coast forest areas between Boston and New York.

Litchfield

Part of the larger Litchfield Hills, this 18th-century town of just under 1,200 people, is notable for its outdoor attractions that offer hiking, boating, and fishing. It is home to Mount Tom State Park, which gives you a great view of Mount Everett, the highest peak in the south Taconics in Massachusetts. Litchfield also contains the White Memorial Conservation Center Museum, which provides an outdoor bird sanctuary, exhibits, and more. For lovers of historic architecture, Litchfield provides plenty of variety with the Milton Historic District and the Topsmead Cottage at Topsmead State Forest.

Barkhamsted

Located within Litchfield County, Barkhamsted is filled with state forest and recreational land, which makes it ideal for a day of hiking and exploring. One of its most picturesque attractions is Samville Dam, a historic dam that resembles the parapet of a medieval castle. It is home to two state forests: Peoples State Forest and American Legion State Forest. The Farmington River in the area is renowned for being a great place to fish for trout. Barkhamstead consists of two villages, Pleasant Vally and Riverton, the latter of which has a main street listed on the National Historic Register for its historic buildings.

Mystic

More than 4,700 people live in this town on the Mystic River, which was first settled in 1654 as a safe harbor for ships. Today, this town is packed full of places to explore and learn, such as the Mystic Seaport Museum, a maritime museum, the Mystic Aquarium and the Museum of Art. The town is full of charm, which is on full display at the open-air Olde Mistick Village, which provides boutiques, theater, and dining. The town is perfect in colder months thanks to B.F. Clyde's Cider Mill, the only steam-powered cider mill in the U.S., offers cider and donuts to customers.

Discover the Hidden Gems of Connecticut

Connecticut may be compact in size, but its small towns pack a punch with their vast array of attractions and activities. From the allure of historic lighthouses and maritime museums to the tranquil beauty of state parks and charming local streets, these nine towns exemplify why Connecticut's lesser-known destinations are deserving of attention. Offering a blend of adventure, history, and scenic beauty, each town invites visitors to experience a side of New England that's rich in culture and charm. Whether you're drawn to outdoor adventures, historical exploration, or simply the pleasure of a quaint village atmosphere, Connecticut's underrated towns are treasure troves of experiences waiting to be discovered.