10 Most Beautiful Small Towns in Connecticut

6: Mystic

Photo Courtesy: Flickr/jjbers

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

7: Madison

Photo Courtesy: Wikimedia/Léo Schmitt

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

8: Weston

Photo Courtesy: Flickr/Doug Kerr

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

9: Greenwich

Photo Courtesy: 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

10: Old Saybrook

Old Saybrook
Photo Courtesy: 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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