The Getaway
Connecticut's Most Charming Small Towns

Want to experience New England charm without the cost and crowds of a big city? Look no further than these small towns in Connecticut. They're a haven for vibrant culture, breathtaking views, rich history, friendly communities, and much more. There's something for everyone, from endless outdoor adventures to culinary delights and unique boutiques. Just be sure to budget extra time — you won't want to leave.

Advertisement

01 Chester

Settled in 1692, this lively town in Middlesex County is in the Connecticut River Valley. It boasts original buildings with stunning architecture, many of which are on the National Register of Historic Places, including the Old Town Hall. Downtown Main Street is the place to be. Grab a bite at Village Tavern, and if you're lucky, snag tickets to a show at the Norma Terris Theater, part of the Goodspeed Opera House. Then visit the Cockaponset State Forest to recharge in nature with hiking, fishing, and biking.

02 Cornwall

Located in northwest Litchfield County, Cornwall borders the Housatonic River in the foothills of the Berkshire mountains. It's where you can experience a slower pace of life alongside a vibrant culture. The West Cornwall Covered Bridge is one of the last remaining covered bridges in the state and tops the list of recommended places to visit.

Cornwall is also Connecticut's greenest town, full of various recreational activities, like fishing, hiking, and rafting, thanks to the Mohawk State Forest. Visiting in the winter? Mohawk Mountain - Connecticut's largest ski area - will not disappoint.

A historic red covered bridge crosses the Housatonic River in West Cornwall, Connecticut on a sunny fall day. Jennifer Yakey-Ault/ Getty Images

03 Chaplin

This quiet, rural town sits in northeastern Windham County and was named after early settler Deacon Benjamin Chaplin; it's home to two sites on the National Register of Historic Places — the Chaplin Historic District and the Witter House. Both are located on Chaplin Street. Find your peaceful oasis by walking on its beautiful hiking trails along the Natchaug River, or go off the beaten path to enjoy a swim in Diana's Pool. Nickerson Park is an excellent option for camping.

Diana's Pool is a section of the Natchaug River where small falls and cascades are present. Patricia Reynolds/ Getty Images

04 Essex

Essex lies in south central Middlesex County, where the Connecticut River empties into the Long Island Sound. Its character comes alive in the town center with small streets lined with shops, galleries, and restaurants. Pop into Cooper & Smith gallery and grab a cozy meal at the Griswold Inn. You can also get a history lesson at the Connecticut River Museum or on a riverboat tour with Essex Steam Train and Riverboat. Finally, save time to relax in nature at its surrounding parks and conservation land.

Fun fact: If you're a Gilmore Girls fan, this is where Stars Hollow was filmed!

05 Kent

This Northwest town in Litchfield County is incredibly rural, with unbeatable scenic views. Visit in the fall to see some of the best foliage in the state. Kent also has must-see history, such as the covered Bulls Bridge — one of the few remaining 19th-century bridges. Outdoor lovers will find a haven at Macedonia Brook State Park and Kent Falls State Park. Book aficionados can peruse House of Books on Main St., and beer snobs can enjoy a taste test at Kent Falls Brewing.

Red covered bridge for pedestrians, Kent Falls State Park, Kent, Litchfield County, Connecticut, USA. Jeff Hunter/ Getty Images

06 Mystic

Located in southeastern New London County, Mystic is everything you would expect from a quintessential New England town. If the name feels familiar, think about the movie Mystic Pizza, starring Julia Roberts. You can eat at the original restaurant. Stroll along Main Street and take in the harbor views as you cross the Mystic River Bascule Bridge. Treat yourself to unique shops, galleries, and seafood restaurants like S&P Oyster. Complete your visit by learning about the town's legacy at the Mystic Seaport Museum or seeing the only beluga whales in New England at the renowned Mystic Aquarium.

Mystic is a village in New London County, Connecticut, in the United States DenisTangneyJr/ Getty Images

07 Madison

This gorgeous beach town in New Haven County will be your next home away from home. Hammonasset Beach State Park is one of the state's most popular attractions and offers two miles of pristine beaches along the Long Island Sound. If you're a nature lover, check out Meigs Point. The Shoreline Greenway trail is perfect for walking, running, biking, or birdwatching. Then, head downtown to shop local boutiques and dine al fresco at Lenny & Joe's Fish Tale or the Clam Castle.

Madison Connecticut West Wharf Beach. Photo by Bob Gundersen/ Getty Images

08 Weston

Due to strict zoning laws, local businesses are at the heart of this Southwestern town in Fairfield County, adding to the small-town charm. It's home to Devil's Den Preserve, the Nature Conservancy's largest preserve in the state. Devil's Den contains woodlands, wetlands, rock ledges, ridges, and valleys. It also offers 20 miles of hiking along diverse plants and wildlife, including the infamous Lucius Pond. Other places of interest include the fascinating 17-acre Coley Homestead, a former working farm, and the Weir Farm National Historic Site, the home and studio of the Impressionist artist J. Alden Weir.

09 Greenwich

An hour from NYC, this wealthy town in Fairfield County became a popular place for relocation during the pandemic, but don't let that discourage you. First, visit the Bush-Holly House at the Historical Society or the Bruce Museum for art and natural history. Then, splurge at high-end shops and restaurants along Greenwich Avenue. Lastly, wind down at the beach at Greenwich Point Park (call it Tod's Point to fit in with the locals).

Greenwich is a town in Fairfield County, Connecticut, United States. DenisTangneyJr/ Getty Images

10 Old Saybrook

Like Essex, this quaint town in Middlesex County is on the Connecticut River. It was settled in 1635, making it Connecticut's oldest town along the shoreline. Find picture-perfect sunset views at Breakwater Lighthouse, where the Connecticut River meets the Long Island Sound. Spend time at Harvey's Beach to feel the soft, white sand between your toes and enjoy fishing, boating, and swimming. Then head to the town center for the historic charm this small town is famous for. Dine on the water at Fresh Salt and catch a performance at The Kate or The Katherine Hepburn Cultural Arts Center.

Lynde Point Lighthouse, Old Saybrook, Connecticut, USA lucky-photographer/ Getty Images
Share

Scroll Down

for the Next Article

The Getaway Badge
Sign up to receive insider info and deals that will help you travel smarter.
Advertisement
Advertisement