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Located in the southwestern corner of the county, Bennington is the most populous town in southern Vermont with approximately 16,000 residents! There are three historic districts within the town today: Old Bennington, Downtown Bennington and North Bennington. Of these, Old Bennington is the original settlement, dating back to 1761 followed by Downtown Bennington in the early 1800’s thanks to ready access of natural resources, waterpower and manufacturing.

In commemoration of the Battle of Bennington, (a pivotal turning point of the Revolutionary War,) you can visit the Bennington Monument, a 306-foot-high (93 m) stone obelisk that is the tallest human-made structure in Vermont. Just around the corner from The Monument, you can walk to the Old First Church and cemetery with graves dating back to the early 1700’s and the final resting place of many Revolutionary War veterans as well as the well-known poet, Robert Frost.

Historic downtown Bennington has something for everyone. Walk our Main Street and visit the Old Castle Theater, Bennington Pottery, The Village Chocolate Shops, plus many more locally owned shops, breweries and cafes.

The Long Trail and Appalachian Trail overlap each other just outside of town and its not uncommon to see thru-hikers enjoying a well-deserved break! A few miles past the LT/AT trail head, you’ll find Prospect Mountain and I guarantee you won’t be able to stop yourself from thinking snow! Because this is one local gem for cross country skiing.

Bennington offers something for everyone….covered bridges, art museum, craft beer, local artisan shops, bowling, movie theatre, scenic drives with good hot coffee…you won’t regret the trip!


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