10 Most Beautiful Small Towns in Connecticut You Should Absolutely Visit

Last Updated on June 26, 2023 by Nikki Jain

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!

Best Small Towns in Connecticut

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1: Chester

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

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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

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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

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

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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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6: Mystic

At one time, Mystic was the most important seaport in the region. Today, it is a major tourist destination. Visitors can enjoy the ocean-side setting of the town and learn about the area’s maritime culture and history. Head to Mystic Seaport, an excellent maritime museum within the town, and check out the historic ships such as the whaleships Charles W. Morgan! You can also enjoy a day at the Mystic Aquarium & Institute for Exploration to learn about marine life and visit the famous beluga whales.

Address: Mystic, CT

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This beachside town is a popular place for people to take camping trips. The lovely natural world of Madison, Connecticut attracts fishers, surfers, picnickers, and more. Here, you can opt to take a beach trip to Hammonasset Beach State Park, Surf Club Beach, East Wharf, or West Wharf. Each of these has its own unique vibe, so you whether you’re loading up your minivan with kids and snacks or taking a solo escape, you’re sure to enjoy Madison’s beaches.

Address: Madison, CT

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Weston is fairly close to New York City—close enough that a good twenty percent of its inhabitants commute every day to work in the Big Apple. However, the feel of Weston is just about as far away from a big city as you can get. It’s little wonder than these commuters opt to live in the beautiful Connecticut countryside! The town is largely residential, with few commercial buildings. It’s also a highly affluent area that is well cared for and filled with wide open spaces and lovely parks. If you visit, you’ll find a handful of lovely historic buildings, beautiful nature preserves, and plenty of places to walk, play baseball, and swim.

Address: Weston, CT

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9: Greenwich

Flickr/Doug Kerr
Another small Connecticut town near New York City is Greenwich. This town is such a nice place to be that Money magazine listed it as the number one place to live in the United States! Over a quarter of this town is composed of water, and much of the town’s land is made up of islands. One of these is a bird sanctuary, but vacationers can visit and enjoy most of the others. Aside from beach and water activities, Greenwich also features many museums, art galleries, and historic areas of interest.

Address: Greenwich, CT

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10: Old Saybrook

Old Saybrook
Flickr/Adam Moss
This small town in Connecticut has been settled for almost 400 years, and it even has its own town seal. Originally a Dutch colony, this town was Anglicized in its later years and still bears vestiges of both European cultures. The town is full of sites on the National Register of Historic Places, including the popular Black Horse Tavern, Lynde Point Lighthouse, and Connecticut Valley Railroad and Turntable Site. If you visit, be sure to make time to visit the beautiful beaches in Old Saybrook as well.

Address: Old Saybrook, CT

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