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October 2019


October 5
Colgate Park, 1357 West Road
Bennington, VT 05201 United States
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octoberfest vermont event bennington pretzel stand

A quintessential Octoberfest set against the backdrop of beautiful of Vermont mountains in their fall foliage glory. Ethnic Food. Beer Tent. Live Music. Artisan Vendors. German DJ. Children’s Activities. Wagon rides. Photo Credit: Lorianna Weathers

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Fallapalooza – Fall Festival

October 26 @ 11:00 am - 3:00 pm
Downtown Bennington Bennington, VT 05201 United States + Google Map
pumpkins vermont fall festival fallapalooza

  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.

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January 2020


January 25, 2020
Lake Paran, Houghton Lane
North Bennington, VT 05257 United States
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gleeful boys sledding winterfest vermont winter festival

  The idyllic Vermont Village of North Bennington is the site of Winter fun for the annual Winter Festival. Come plunge in icy waters in the Penguin Plunge Event.

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March 2020

Winters Wings and Home Brew Festival

March 7, 2020
Downtown Bennington Bennington, VT 05201 United States + Google Map

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.

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Vermont Maple Open House Weekend

March 21, 2020 - March 22, 2020
vermont maple syrup pancakes

Celebrate the start of maple season in Vermont. Maple syrup farms throughout Bennington County open their doors to visitors to sample the first delicious crop of the season and see how the sweet, sticky liquid is made.  Fun for all ages. Photo Credit: The Yellow Note

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May 2020

Mayfest Arts and Craft Festival

May 23, 2020 @ 10:00 am - 5:00 pm
Downtown Bennington Bennington, VT 05201 United States + Google Map

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 things to do and delicious food to eat.

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August 2020

Bennington Battle Day Celebration and Parade

August 16, 2020
Monument Circle Old Bennington, VT 05201 United States + Google Map

This is a weekend long celebration commemorating the Battle of Bennington which took place on August 16, 1777. It was a pivotal Revolutionary War battle which changed the course of history. Weekend events include a war re-enacter encampment at the Bennington Monument, a 5K race, a presentation by the Moodus Drum Fife & Drum Corps, a historic walk in Old Bennington, and a parade in downtown Bennington. Additional details on the Bennington Monument website. Photo Credit: Lorianna Weathers

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