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, Connecticut

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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.

Where to stay: Best Hotels in Connecticut (CT)
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15 Best Small Towns to Visit in Connecticut:

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