Although it’s the third smallest state in the USA, Connecticut certainly punches above its weight when it comes to interesting places to visit. This small New England state just so happens to be one of the country’s oldest states, too, and as such is rich in history and culture.
While visitors are usually tempted to spend their time in the state’s larger urban centers like Bridgeport and New Haven, dig a little deeper and you’ll find numerous small towns radiating their own distinctive charm and character. From coastal villages steeped in maritime legacies to quaint hamlets that bore witness to pivotal moments of the American Revolution, these unique towns stand out as must-visit destinations in the Constitution State.
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Kent
Tucked up against the border with Upstate New York and only a two-hour drive north of NYC, the small community of Kent is valued for its unique blend of cultural attractions and nature. Boasting one of Connecticut’s prettiest little downtown cores, here you’ll enjoy strolling past an array of old architecture that has in some cases been given unique modern twists, reflecting Kent’s vibrant arts and culture community.
It's a scene that’s even more attractive in the fall when visitors flock to Kent for its vibrant foliage displays, especially in nearby Kent Falls State Park. Widely considered the region’s natural crown jewel, have your camera ready for spectacular Kent Falls itself. Connecticut's highest waterfall, it provides an idyllic setting for picnics, hiking... and selfies.
Stonington
Stonington, on Connecticut’s beautiful southeastern coast, boasts a rich seafaring heritage. Founded way back in 1662, much of the town’s 18th and 19th-century architecture has been preserved and is fun to view while exploring its leafy neighborhoods.
Be sure to visit the Stonington Harbor Light. This historical lighthouse dates back to 1840 and, along with its fascinating museum, can be enjoyed for an admission fee of just $5. The nearby Mystic Seaport showcases New England's maritime legacy and is home to the Charles W. Morgan, built in 1841 and the world's last wooden whaling ship.
Essex
Essex, a quaint town set on the banks of the Connecticut River just a few miles inland from Long Island Sound and the Atlantic Ocean, is another pretty coastal community famed for its picturesque landscapes and rich maritime history. While once the community’s harbors bustled with shipbuilding, especially during the War of 1812, today they’re used largely for pleasure boating and are endless fun to wander.
The town’s unique appeal is heightened by the nearby Gillette Castle State Park. Perched atop Seventh Sister Hill, this mock castle was built by actor William Gillette between 1914 to 1919 and offers panoramic views of the river.
Old Lyme
Known as a haven for artists and creative types and named after the historic port town of Lyme Regis in Dorset, England, Old Lyme lays claim to being the birthplace of the American Impressionist movement. This unique legacy is celebrated in the Florence Griswold Museum, a former boarding house for artists that now displays numerous Impressionist works of art.
Nature enthusiasts will appreciate Old Lyme’s close proximity to the Great Island Wildlife Area. This vast tidal marsh showcases a diversity of bird species in their natural estuarine habitats and is a great spot for birdwatching.
Litchfield
Popular for its mix of attractive historical buildings and pretty nature trails, Litchfield is the embodiment of New England’s old charm. Less than an hour’s drive west of Hartford, its central green space wouldn’t look out of place in a picturesque English country village and is surrounded by homes that once belonged to patriots of the American Revolution.
Be sure to also pop into the nearby White Memorial Conservation Center. Covering an area of over 4,000 acres, this area of outstanding natural beauty includes woodlands and watercourses, making it a perfect spot for hiking, bird watching, and nature studies.
Chester
A blend of artistry and riverside charm just a few miles to the north of Essex, Chester is a hive of creativity. You’ll see evidence of Chester’s vibrant visual arts community everywhere, especially in its many downtown galleries and studios. Prefer performance art? Check out the regular live performances at the Norma Terris Theatre, part of the historic Goodspeed Opera House.
After exploring Chester’s historic Main Street visit the Cockaponset State Forest. An easy 10-minute drive north of the town center, it’s the second-largest forest in Connecticut and offers hiking trails, fishing areas, and plenty of opportunities to reconnect with nature.
Suffield
Located in north-central Connecticut and just minutes away from the state border with Massachusetts, Suffield is where you’ll find numerous well-preserved old colonial homes dotted across the area’s rich farmlands. The town’s agricultural roots are everywhere evident, especially if you visit during the Suffield on the Green festival. This fun annual event celebrates the community’s rich cultural and farming heritage.
Just five miles away are the Congamond Lakes, a trio of freshwater lakes that provide residents and visitors with ample opportunities for boating, fishing, swimming, and other water-based activities. It’s also a great spot for a picnic and birdwatching.
Deep River
A former economic powerhouse that once processed an estimated 90 percent of America’s ivory import trade, Deep River today is a quiet spot that makes for a fun day trip. Set on the banks of the Connecticut River, you can easily stroll the quaint downtown area with its boutiques and galleries before taking a rest at the riverfront.
If you can, try to time your visit for the annual Fife & Drum Ancient Muster. The largest gathering of its kind in the world, you’ll be treated to thrilling displays and parades featuring participants from across the globe. Close by, the Selden Neck State Park, an island on the Connecticut River, offers camping experiences and several hiking trails.
The Final Word
Venture beyond the cities and suburban sprawl of New England and you’ll find countless small towns in Connecticut that are busting at the seams with charm and history. These quaint communities, the hidden gems of the Constitution State, boast stunning scenery and quiet streets that are just waiting to share their stories of times gone by with you.
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