15 Best Small Towns to Visit in Connecticut

Connecticut is the southernmost state in New England, and very close to big-city destinations like New York City. Home to Yale University, this state manages to preserve some beautiful colonial history in its small, rural towns. Get in the car and head out on the back roads to discover what Connecticut has to offer – the scenery along the way will impress you with the beautiful mountains and hills, and foliage.

We’re excited for you to discover this New England small-town charm in our list of the 15 best small towns in Connecticut!

1. Chaplin, Connecticut

Chaplin is located in Windham County, and is named after one of its first settlers, Deacon Benjamin Chaplin. Their main street, Chaplin Street, is a designated Historic Place on the National Register of Historic Places. Come visit this quaint town to curl up in their picturesque library, or to hit the trails around town on foot or horseback!

While you are here, stretch your legs and trek out to Diana’s Pool, a gorgeous nature spot that you’ll fall in love with. Or, if you’re more in the mood for comfort food, try Bach Dor Cafe, a perfect pit stop to indulge your love of fried food. Relax at Passport Inn & Suites and let Chaplin take you back to a simpler time.

2. Colebrook, Connecticut

Located in Litchfield County, Colebrook gets its name from Colebrook County, England. A true small New England town, it is ideal to get away from the stress of everyday life and get back to the basics. Wander the picturesque town, chat with the locals, and stop in at Rock Hall, a Historic Place on the National Register.

This town is at its best during the 4th of July festivities, so be sure not to miss out! You can check out the Colebrook Store for some delicious food that some call “edible history”. Treat yourself to a weekend away at Rock Hall Luxe Lodging and enjoy some time to yourself.

3. Columbia, Connecticut

A town located in Tolland County, Columbia is named after the American ballad Hail, Columbia. Its Columbia Greene Historic District was listed on the National Register of Historic Places, and is well worth your time to explore. The old stone buildings date from the early 19th century and are surrounding a beautiful green that will whisk you away to centuries past.

A perfect stop off the highway, Columbia is bordered by gorgeous nature walks and trees for miles. The town also boasts an excellent train museum. We recommend stopping in during the summer, because the town offers passes to non-residents for summer activities – grab a kayak and have some fun! Indulge yourself with something sweet at Motta’s Pastry & Bake Shop Inc. before continuing on your way.

4. Cornwall, Connecticut

Cornwall is located in Litchfield County, and is a quaint destination sure to enchant you. The poet, Mark Van Doren, wrote a poem about the “Hills of Little Cornwall”, describing the idyllic natural beauty that could be found in the countryside surrounding the town. We recommend a visit especially in autumn to see the colors in all their glory!

Whether or not you’re adventurous enough to strike out into the countryside outside Cornwall, the town itself is also well worth your time. Walk out to the West Cornwall Bridge, one of the few covered bridges in the area. Its red wood is a stark contrast to the greenery surrounding it, so don’t forget your camera. Or, wander town to appreciate the cute buildings reminiscent of gingerbread houses. Enjoy a cup of coffee at Wandering Moose Cafe and stop in at Berkshire Country Store before leaving.

5. Cromwell, Connecticut

Cromwell is located in Middlesex County, near the center of Connecticut. It was named after a boat that sailed along the Connecticut River that was named after Oliver Cromwell. This historic New England town has two separate historic districts, Main Street Historic District and Middletown Upper Houses Historic District, as well as the Sage-Kirby House. Come visit to get a feel for authentic New England old-time towns.

Bring your walking shoes and hit River Highlands State Park. You’ll love the greenery and peaceful view of the river. Or, head out to Cromwell Meadows Wildlife Management Area and explore! Bring your camera and check out the multitude of birds if you’re a bird-watching enthusiast! Take some time to enjoy a meal at Ambrosia and relax.

6. Essex, Connecticut

Located in Middlesex County, Essex is a historic town – it as one of the few American towns to be attacked by a foreign country. During the War of 1812, British vessels arrived and commandeered the town. No casualties were incurred but there were some expensive damages thanks to British looting. Essex survived this and came back strong – it is so beautiful that it was one of the main inspirations for “Stars Hollow” in Gilmore Girls!

Come visit Essex to see a still-running steam train, or stay at one of the oldest inns still in existence, the Griswold Inn. Visit the Essex Library Association to catch up on reading or treat yourself to a day at the Spa of Essex. Have a drink at the Black Seal or enjoy a meal at Olive Oyl’s. Enjoy the taste of history here in Essex, it won’t disappoint you!

7. Kent, Connecticut

Kent is located in Litchfield County, and was founded in 1737. Part of iron production initially, Kent is traversed by the Housatonic River; the town is also home to a historic covered bridge, Bulls Bridge. There is also the Schaghticoke Reservation nearby, and a part of the Appalachian Trail!

Come visit this town and get back in touch with nature! Macedonia Brook State Park is a perfect location for hiking, camping or picnics. Enjoy views of the Catskill Mountains and Taconic Mountains. Or, head out to the waterfall paradise that is Kent Falls State Park. You can even go fishing here and catch the trout brought in from state hatcheries. Head back into Kent to appreciate the antique shops and boutiques, or recharge at the Fife n’ Drum Restaurant.

8. Madison, Connecticut

Madison is located in New Haven County, right on the shore of the Long Island Sound. It was settled in 1641, and declared a town in 1826, making it unofficial rivals with Guilford, the town from which Madison split. Come sneak away to Madison’s beaches for a relaxing, seaside vacation.

Check out Hammonasset Beach State Park for a picnic, nap, or camping. You can fish off the pier here as well. Or, play a volleyball game at Surf Club Beach or take out a sailboat on the water. Enjoy a good meal and unique atmosphere at RJ Julia Booksellers, and pamper yourself at Quiet Cove Massage Therapy. Enjoy a few days at Scranton Seahorse Inn and let the sea breeze rejuvenate you. You’ll feel like a new person.

9. Monroe, Connecticut

Located in Fairfield County, Monroe is close to bustling big cities like New York City, but far enough away that you still have the peace and quiet of the country. The town gets its name from James Monroe, the fifth president of the US. A town that still looks like it is from the colonial times, take a quick trip away and stop here to recharge your batteries.

Bring your bike and hit the trails here – there are many bike paths for aspiring cyclists. Or, stay in town and spend some time becoming a beer connoisseur at Veracious Brewing Company. You can sober up over a cup at Last Drop Coffee Shop before walking around and enjoying the scenic town. Enjoy a good meal at Carl Anthony’s Trattoria and take the time to breathe now that you’ve left your worries behind in the big city.

10. Mystic, Connecticut

Mystic is located in New London County. Mystic is unique – it has no independent government as it is not officially recognized as a separate municipality. A whimsical sounding name, they actually say that “Mystic” was derived from the Native American term “missi-tuk” that referred to a large river, a suitable name given the town’s important seaport in colonial times.

Historically significant because of its seaport, the town has commemorated this history at their maritime museum, where you can see the preserved sailing ships. You can also visit the Mystic Aquarium and Institute for Exploration, or watch beluga whales. Wander historic Downtown Mystic, and enjoy some fresh seafood at S & P Oyster Co. Have a slice at Mystic Pizza, inspiration for the movie by the same name starring Julia Roberts!

11. Niantic, Connecticut

Located on the Long Island Sound on the Niantic Bay, this village is a seaside resort destination. Named after the Niantic People, the tribe inhabited Connecticut and Long Island before the areas were settled by the Europeans. Niantic is ideally situated next to the water and is also surrounded by beautiful nature, making it an ideal vacation spot for anyone.

Come visit and spent some time sailing on the bay. Head out to the mile-long beach at Rocky Neck State Park, or row out to some of the tiny islands dotting the coast, like Gardiners Island. You can camp here in the summer or hike in the woods in the off-season. While a great summer destination, there is something to do here for all seasons. Check out the books at the Book Barn and wander the shops on Main Street. Enjoy a few days off at the Inn at Harbor Hill Marina and let the sounds of the ocean soothe you.

12. Old Saybrook, Connecticut

Old Saybrook is located in Middlesex County, and was founded in 1635 at the mouth of the Connecticut River. The Fort controlled the main trade and supply route to the upper river valley, and the Collegiate School of Connecticut was first chartered in Old Saybrook. The school was later moved to New Haven, was renamed Yale University.

Treat yourself and visit Yale’s birthplace when you make a reservation at Saybrook Point Inn & Spa. Walk along Harvey’s Beach or play a round of golf at Fenwick Golf Club. Check out the Lynde Point Lighthouse or go antiquing at Long Ago Antiques. Enjoy the food at Liv’s Oyster Bar & Restaurant and after, have a quiet drink at Fresh Salt.

13. Putnam, Connecticut

Putnam is in Windham County and was named after Revolutionary War General Israel Putnam. The town grew around the clothing mill industry, and was a key contributor in making clothes for Civil War soldiers. Come visit this small New England mill town.

Catch a show at the Bradley Playhouse, or go antiquing at Jeremiah’s. Get back in touch with your artistic side at Artique – a Paint Bar, or check out the unique instruments at String Tinkers. Relax at the upscale inn, Whitehaven, and sit down for a leisurely eating experience at 85 Main. We recommend saving room for dessert at Victoria Station Cafe!

14. Washington, Connecticut

A rural town in Litchfield County, Washington is a town known for rubbing shoulders with New York City and well known for its lovely countryside, historic architecture and bustling cultural life. Located in the foothills of the Berkshire Mountains, many locals can trace their ancestry back to the Colonial period.

Bring your walking shoes and head out to the Shepaug River which winds through Hidden Valley Preserve. Or, visit the second largest natural lake in Connecticut, Lake Waramaug – bring your camera, it’s very scenic. If you’re staying in town, spend some time at Hickory Stick Bookshop or Hollister House Garden. Put your feet up at the Orange Gild Bed and Breakfast, and treat yourself to an upscale eating experience at the Mayflower Dining Room.

15. New Milford, Connecticut

New Milford is located in Litchfield County, on the Housatonic River. The area was previously inhabited by the Weantinock Native Americans, a subgroup of the Paugusset, who farmed and fished here before the arrival of John Noble in 1707, who established a small community there. The town later participated in the American Revolution by sending the 7th Connecticut Regiment to fight in battles such as the Battle of Brandywine.

Come visit this town and pay a visit to Lovers Leap State Park, or Harrybrooke State Park – both are perfect for either a relaxing picnic or a hike. Pick up a hobby and take a cooking class at the Silo Cooking School, or visit the Village Center for the Arts. Try the sushi at Yokohama or disconnect from normal life at Homestead Inn. You deserve the quiet rest!