Walkable Town Centers Last Updated: March 2021

Sometimes it’s nice just to get out of the car or off the train and walk. Connecticut has many town centers where a nice ramble takes you to shops, restaurants, galleries, museums and even a park bench or two. Here are some of the best ones to consider for a day of safe, leisurely exploration.

Just be sure to check with each location before venturing out as hours may change due to COVID-19.

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With a Main Street that’s over a mile long, the colonial town of Ridgefield boasts unique eateries and boutiques. A handful of interesting museums, which hold tours daily, are located in its vibrant downtown.

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West Hartford Center

The intersection of Farmington Avenue and South Main Street in West Hartford can lead you to many shopping or dining pleasures, and eventually to the adjacent Blue Back Square.

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New Canaan

This classic commuter town has an appealing downtown and many restaurants, especially in the triangle formed by Main, Locust and Forest Streets. Lots of places to shop, too.

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New Haven

There's so much to see and do in New Haven — all in a walkable setting! Stroll the New Haven Green and pop in the Shops at Yale. You're sure to find many dining options as well, including the #1 rated pizza in the U.S.

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If it’s small-town charm you’re looking for, you won’t find a better destination than Chester, in the Lower Connecticut River Valley. Galleries, tasteful little shops and an interesting variety of restaurants.

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Greenwich Avenue, Greenwich

A shopping mall would never do in affluent Greenwich, not when there’s fabulous Greenwich Avenue and its array of shops and restaurants running between Route 1 and Bruce Park Avenue. Don't miss the annual Greenwich International Film Festival held in eary June, all events associated with the festival are all in walking distance and some close to the train station.

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Perfect for browsing or a bite to eat, Litchfield’s West Street borders the village’s historic town green. Shop for everything from antiques to gourmet gifts while enjoying the scenery at this quintessential 18th century New England town.

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If you’re looking to shop and stroll near the water, State Street in downtown Westport is a fantastic spot for a day trip. Stretch your legs as you explore its multiple mom-and-pop shops, unique restaurants, galleries and landmarks.