Walkable Town Centers Last Updated: June 2022

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.

Planning how to get there? Choose a greener way to travel. See all the transportation options near you with the CTrides transit finder.

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Putnam

Discover the quaint town of Putnam in Connecticut’s Quiet Corner. Best known as an antiquing destination, the not-so-sleepy town offers a flourishing downtown with cafes, galleries, and shops.

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Ridgefield

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 & Blue Back Square

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. Find more ways to enjoy West Hartford here.

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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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Chester

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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Litchfield

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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Westport

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.

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New Milford

Discover an authentic blend of small town and country living offering wonderful shops and restaurants in this historic New England village. Enjoy a quaint town green, home to many monuments and civic structures, including a bronze bust of Abraham Lincoln, an Army tank and a bandstand.

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Manchester

Manchester has the perfect blend of small town feel with big city convenience. Just a short drive outside of the capitol city, Manchester offers plenty of shopping, dining and attractions for all to enjoy. Discover trendy breweries, street art, and even attend Downtown Manchester, a monthly event to encourage people to visit all the walkable places on Main Street.