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Fallapalooza – Fall Festival

Downtown Bennington Bennington

  Live music and fun for the whole family as we wave goodbye to another beautiful Vermont foliage season. Join the celebration where main street is blocked off for the fun and festivities.

Bennington Community Theatre — 2019 Season

Who'd have thought that so much talent could be packed into one tiny Vermont town? From comedy's to dramas to classics, Bennington's Community Theatre delivers first rate performances in the beautiful Oldcastle Performing Arts center in downtown Bennington, Vermont.

$10 – $15

Bennington Musuem Events – 2019 Season

Bennington Museum 75 Main Street, Bennington

The Bennington Museum offers world-renowned, visiting exhibitions, holiday parties, children's activities and so much more. Explore their list of events for the full year and plan your trip to Bennington, Vermont.

Home for the Holidays Series – Annual December Events

Downtown Bennington Bennington

From hometown tree lighting celebrations, to brunch with Santa, to Family Festival Day at the Bennington Museum to holiday concerts and more. Bennington is brimming with holiday cheer from the first to the 31st of December. The Bennington area Chamber of Commerce has assembled an itinerary of the cheeriest of the cheery for you and

Bennington County’s Got Talent

bennington college Greenwall Auditorium, VAPA, Bennington

3rd annual Talent Show in Bennington Vermont. Talented contestants of of all ages compete for a $1,000 prize. A great night of fun and entertainment.

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 will warm even the coldest winter day. And help decide who will be crowned the winner of the Best Wings in Bennington.

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 deals while downtown stores open their doors until midnight. And don’t forget to check out Four Corners North, where Hawkins House, Tap House at Catamount

Learn about more community events at the Bennington Area Chamber Calendar