10 Most Beautiful Small Towns in Connecticut

Connecticut is the ideal place to tour quintessential New England small towns. The communities in Connecticut are characterized by colonial architecture, historic sites, and stunning natural areas. Many of the most beautiful small towns in Connecticut are bordered by nature preserves or beaches—or both! If you love history and nature, you can get the best of both worlds in small town Connecticut!

1: Chester

Photo Courtesy: Flickr/Doug Kerr

Chester is an excellent place to go if you want to enjoy lovely sights and that quiet, small-town feel. This historic town is located in a place that has been inhabited since long before Europeans landed on the American continent. When you visit, you’ll see why this has always considered been a great place to live! Surrounding the town, Cockaponset State Forest offers the traveler endless diversions, such as hiking, cycling, and camping. You can also visit Selden Neck State Park, or take a walk around town and enjoy the beautiful architecture. Be sure to see Gillette Castle!

Address: Chester, CT

2: Cornwall

Photo Courtesy: Wikimedia/Joe Mabel

This lovely little community offers everything we love about small town Connecticut: old covered bridges, rolling hills, and historic architecture. Cornwall is most popular for its ski opportunities. Mohawk Mountain Ski Area is a great place to visit in winter if you enjoy all kinds of winter sports! In the summer, you can visit Mohawk Mountain State Park to enjoy the sunny forested area around Cornwall.

Address: Cornwall, CT

3: Chaplin


Imagine an East Coast town characterized by red brick, spacious lawns, and trees that turn a thousand shades of orange each autumn. This may sound like many small towns in Connecticut, but Chaplin is especially lovely. The town is well cared for, and it features many lovely homes scattered among the trees. The town has two notable historic places: Chaplin Historic District and Witter House. These are filled with mostly Georgian architecture from the early 19th Century.

Address: Chaplin, CT

4: Essex

Photo Courtesy: Flickr/Doug Kerr

In the history books, Essex is known as one of the towns attacked in the War of 1812. However, today’s Essex is about as peaceful as it gets. The most notable historic architecture dates to the 19th Century and lends an old-fashioned air to the area. History and art lovers will enjoy the museums in the town, including the Connecticut River Museum, the Cooper & Smith Gallery, and the Essex Art Association Gallery. One of the most popular attractions in town is the Essex Stream Train, which takes visitors along a scenic route from Essex to Deep River.

Address: Essex, CT
Website: www.essexct.com

5: Kent

Photo Courtesy: Flickr/Bob P. B.

Kent may be a small town, but it offers plenty to do and see! It’s near two different state parks, Macedonia Brook State Park and Kent Falls State Park. If you visit, you can enjoy wandering along the wooded paths and staring in awe at the beautiful water falls. Kent is also home to one of Connecticut’s few remaining 19th Century covered bridges, Bulls Bridge. The site of the bridge is the place where George Washington crossed the river in 1781.

Address: Kent, CT

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