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Hemmings Cruise-In

Downtown Bennington Bennington, VT

Hemmings Cruise-Ins are back! In association with the Better Bennington Corporation, we will be hosting our popular cruise-ins on Main Street in Bennington, VT.  The street will be closed for these events. Bring your collector car and join us!

Food Truck Festival – Annual Event

Downtown Bennington Bennington, VT

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

Bennington Performing Arts Center

Downtown Bennington Bennington, VT

Bennington Performing Arts Center — The Home of Oldcastle Theatre Company — is restarting their programming beginning Friday, September 11, 2020. Live theater and performing arts in beautiful downtown Bennington Vermont. Visit the website (below) for a complete calendar of live theater, performing arts, camps and more. Located in the heart of Bennington's downtown shopping

Midnight Madness – Annual Event

Downtown Bennington Bennington, VT

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

Winters Wings and Home Brew Festival

Downtown Bennington Bennington, VT

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.

Home for the Holidays Series – Annual December Events

Downtown Bennington Bennington, VT

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

Fallapalooza – Fall Festival

Downtown Bennington Bennington, VT

  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.

Learn about more community events at the Bennington Area Chamber Calendar