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Oldcastle Professional Theater 2020 Season

Downtown Bennington Bennington

Live theater and performing arts in beautiful downtown Bennington Vermont. Visit the Oldcastle website for a complete calendar of live theater, performing arts, camps and more. Located in the heart

Winters Wings and Home Brew Festival

Downtown Bennington Bennington

Micro Brews, home brews are all the rage. And Bennington Vermont’s HomeBrew Festival gathers together a whole array of top notch home breweries and micro breweries for a party that

Mayfest Arts and Craft Festival

Downtown Bennington Bennington

Mayfest is an annual street fair held in downtown Bennington featuring a wide variety of arts, crafts, activities, food, and entertainment. Families and people of all ages will find fun

Midnight Madness – Annual Event

Downtown Bennington Bennington

Come join the fun for Bennington’s annual Midnight Madness event — 56 years and running! Bennington’s entire downtown main street is all abuzz with live music, great food, and amazing

Bennington Arts Weekend – Annual Event

Downtown Bennington Bennington

It’s no wonder Bennington hosts the annual Arts and Craft show. After all Bennington was ranked in the top ten most vibrant arts communities by SMU’s National Center for Arts

Food Truck Festival – Annual Event

Downtown Bennington Bennington

Just like it sounds! Head downtown where streets are blocked off for a food truck extravaganza. And a beer garden too. Photo Credit: Lorianna Weathers

Learn about more community events at the Bennington Area Chamber Calendar