Connecticut, the southernmost state in New England, is not just about big cities like New York City. It is also home to some beautiful colonial history preserved in its small, rural towns. The scenic back roads of Connecticut will impress you with stunning mountains, hills, and foliage. So, hop in your car and explore the charming small towns that Connecticut has to offer. In this article, we’ll take you on a journey through the 15 best small towns in Connecticut, each with its own unique charm and attractions.
1. Chaplin, Connecticut
Chaplin, located in Windham County, is a quaint town with a rich history. Named after its first settler, Deacon Benjamin Chaplin, this town is a designated Historic Place on the National Register. Chaplin Street, the main street, is a picture-perfect spot to explore. Visit Diana’s Pool for nature trails or indulge in comfort food at Bach Dor Cafe. Relax at Passport Inn & Suites and let Chaplin take you back in time to a simpler era.
- Things to do in Chaplin:
- Visit Diana’s Pool for nature trails.
- Try comfort food at Bach Dor Cafe.
- Relax at Passport Inn & Suites.
2. Colebrook, Connecticut
Colebrook, located in Litchfield County, is a small New England town where you can escape the hustle and bustle of everyday life. Wander through the picturesque town, visit Rock Hall, and enjoy the 4th of July festivities. Don’t miss the delicious food at the Colebrook Store, known for its “edible history.” Stay at Rock Hall Luxe Lodging for a weekend getaway.
- Must-visit in Colebrook:
- Enjoy the 4th of July festivities.
- Check out the Colebrook Store for tasty food.
- Stay at Rock Hall Luxe Lodging.
3. Columbia, Connecticut
Columbia, located in Tolland County, is a charming town with a rich history dating back to the early 19th century. The Columbia Greene Historic District is a must-visit for history enthusiasts. Explore the beautiful green surrounded by old stone buildings. During summer, enjoy summer activities like kayaking with passes available for non-residents. Treat yourself to something sweet at Motta’s Pastry & Bake Shop Inc.
- Explore Columbia:
- Visit Columbia Greene Historic District.
- Enjoy summer activities like kayaking.
- Indulge in sweet treats at Motta’s Pastry & Bake Shop Inc.
4. Cornwall, Connecticut
Cornwall, located in Litchfield County, is a quaint destination known for its natural beauty. Visit the West Cornwall Bridge, one of the few covered bridges in the area, and explore the countryside. Enjoy the colorful foliage in autumn and wander through the town’s gingerbread house-like buildings. Stop for coffee at Wandering Moose Cafe and visit Berkshire Country Store for a unique shopping experience.
- Highlights of Cornwall:
- Visit the West Cornwall Bridge.
- Explore the gingerbread house-like buildings.
- Stop at Berkshire Country Store for souvenirs.
5. Cromwell, Connecticut
Cromwell, located in Middlesex County, is a historic New England town with two separate historic districts. Explore the Main Street Historic District and Middletown Upper Houses Historic District, and visit the Sage-Kirby House for a glimpse of authentic New England history. Take a stroll through River Highlands State Park or Cromwell Meadows Wildlife Management Area for a peaceful outdoor experience. Enjoy a meal at Ambrosia and relax in this charming town.
- Enjoy Cromwell’s Charm:
- Explore historic districts.
- Visit River Highlands State Park.
- Indulge in a meal at Ambrosia.
6. Essex, Connecticut
Essex, located in Middlesex County, is a historic town famous for surviving an attack during the War of 1812. Visit the Griswold Inn, one of the oldest inns in existence, or explore the Essex Library Association for some quiet reading time. Treat yourself to a spa day at the Spa of Essex or enjoy a drink at the Black Seal. Don’t miss a meal at Olive Oyl’s, and immerse yourself in the town’s rich history.
- Unwind in Essex:
- Visit the Griswold Inn.
- Relax at the Spa of Essex.
- Enjoy a meal at Olive Oyl’s.
7. Kent, Connecticut
Kent, located in Litchfield County, is a town steeped in history and natural beauty. Explore Macedonia Brook State Park or Kent Falls State Park for outdoor adventures. Take a walk on Bulls Bridge, a historic covered bridge, and admire the picturesque views.
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