7 Playfully Peculiar Towns In Connecticut

Connecticut may be famous for its polished coastal communities and classic New England scenery, but some of its smallest towns have personalities that are anything but ordinary. In Essex, visitors can ride a vintage steam train before boarding a riverboat on the Connecticut River. Kent still sends cars across an 1842 covered bridge, while Chester has a historic ferry and a farm full of alpacas. Putnam hides a waterfall beside old mill buildings, and Stonington turned an 1840 lighthouse into what is billed as America’s first lighthouse museum. These seven towns pair classic New England charm with the kinds of odd landmarks, old traditions, and unexpected attractions that make a detour worthwhile.

Essex

This feels like the kind of town that was designed for a postcard. With a population of roughly 6,700, it combines a picturesque waterfront with historic buildings, independent shops, restaurants, and marinas. Visitors can stroll through Essex Village, explore the Connecticut River Museum, browse the local shops, and take in views along the Connecticut River. The town's most distinctive attraction, however, is the Essex Steam Train & Riverboat, where an old-fashioned train ride can be combined with a cruise aboard the Becky Thatcher riverboat.

That train-and-boat combination is what makes Essex particularly playful and unusual. Instead of simply sightseeing from a train or a boat, visitors get both experiences during one journey through the Connecticut River Valley. The restored 1892 Essex Station adds even more vintage charm.

Kent

This is a small Litchfield County town of roughly 3,000 people, but it packs plenty of scenery and character into its rural landscape. Visitors can explore the walkable downtown, browse independent shops and galleries, hike around Bulls Bridge, and visit Kent Falls State Park. Kent Falls is particularly impressive, with a series of cascades dropping dramatically through a wooded landscape. The town is also surrounded by opportunities for hiking, fishing, and enjoying the Housatonic River.

The wonderfully peculiar feature here is Bulls Bridge, a historic covered bridge built in 1842 that stretches 109 feet across the Housatonic River. It is not just something to photograph from a distance; visitors can actually drive across it and explore the surrounding trails and river scenery.

Chester

With a population of only about 3,700, Chester is tiny even by Connecticut standards, but its personality is much bigger. The town's curved Main Street is filled with historic buildings, independent shops, restaurants, and galleries, making it an easy place to explore on foot. Visitors can browse the downtown shops, visit the Chester Museum at the Mill, explore nearby Cockaponset State Forest, or spend time at Cedar or Pattaconk Lake. The town also has a particularly unusual way to get around: the Chester-Hadlyme Ferry carries vehicles across the Connecticut River and provides an attractive approach to Gillette Castle.

The ferry is one of Chester's most peculiar attractions because it has been operating for generations and is one of Connecticut's remaining historic ferries. Another fun stop is Chakana Sky Alpacas, where visitors can see alpacas and shop for alpaca products.

Putnam

This town, with a population of roughly 9,200, has reinvented itself from an old mill town into an eclectic destination filled with antiques, art, restaurants, theaters, and outdoor recreation. Visitors can browse the enormous Antiques Marketplace, walk the Putnam River Trail, explore downtown shops and galleries, or catch a performance at the historic Bradley Playhouse. The Quinebaug River also runs through town, adding water views and walking opportunities to the downtown experience.

Putnam's unusual side comes from the way its industrial past blends with its modern arts scene. One of the most unexpected sights is Cargill Falls, a waterfall tucked into the downtown area near historic mill buildings. The town was also once known as the "Antiques Capital of the East," and its Antiques Marketplace contains hundreds of dealer spaces spread across multiple floors.

Wethersfield

This town is larger than the other towns on this list but still has only around 27,000 residents, keeping it well below the series' 50,000-person limit. Its historic center, Old Wethersfield, is filled with centuries-old homes, museums, shops, churches, and tree-lined streets. Visitors can walk the three-mile Wethersfield Heritage Walk, explore the Webb-Deane-Stevens Museum, visit the Broad Street Green, or relax around Wethersfield Cove.

The town's peculiar claim to fame is its Cove Warehouse, a remarkably old riverfront building connected to Wethersfield's historic maritime trade. The warehouse dates to the late 17th or possibly 18th century and was once part of a larger group of warehouses along the river. Another quirky part of Wethersfield's history is its connection to the region's onion-growing and trading past.

Guilford

This town is a coastal town of about 22,000 people where history and seaside scenery come together. Visitors can stroll around the Guilford Green, explore the Henry Whitfield State Museum, spend time at Jacobs Beach, or hike through the preserves such as Bluff Head. Chaffinch Island Park is another beautiful stop, offering views of Long Island Sound and Faulkner's Island. The town also has historic homes, small shops, restaurants, and opportunities for kayaking and other outdoor activities.

The truly peculiar attraction is the Henry Whitfield House, a massive stone building dating to the 1600s that is recognized as the oldest house in Connecticut and the oldest surviving stone house in New England. That makes it an especially memorable landmark in a town otherwise known for beaches and coastal scenery. Guilford also has the Dudley Farm Museum, a living-history site where visitors can see an old working farmstead and learn about rural life.

Stonington

This is a coastal town of fewer than 20,000 residents with a particularly picturesque historic borough. Visitors can walk along the waterfront, explore the historic village streets, visit the Captain Nathaniel B. Palmer House, and enjoy the area's shops and restaurants. The town's coastal setting also provides plenty of opportunities for harbor views, boating, and scenic photography.

The town's most unusual feature is the Stonington Lighthouse Museum, which Historic Stonington describes as America's first lighthouse museum. Built in 1840, the stone lighthouse eventually became a museum in 1927, and visitors can climb its tower for views across Long Island Sound and toward three states. That combination of a historic lighthouse, maritime artifacts, and sweeping coastal views makes Stonington particularly distinctive.

Connecticut's smaller towns prove that you do not need a huge population or a famous city skyline to have an unforgettable travel experience. Chester has a historic river ferry; Essex combines a steam train with a riverboat; Kent has a covered bridge and cascading waterfalls, and Putnam hides a waterfall among its old mill buildings. Each destination offers its own combination of history, scenery, and wonderfully unexpected attractions.

For travelers who enjoy destinations with a little personality, Wethersfield, Guilford, and Stonington are equally worth exploring. From an old maritime warehouse and an ancient stone house to America's first lighthouse museum, these towns have plenty of stories and sights that feel different from the standard Connecticut getaway.