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January 2020

Oldcastle Professional Theater 2020 Season

January 2 - December 31
Downtown Bennington Bennington, VT 05201 United States + Google Map
bennington live theatre my fair lady actors

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 of Bennington's downtown shopping and dining district. Just a short drive from Albany and the Berkshires. Make a date night of it!

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Southern Vermont Storm Football – 2020 Season

January 3, 2020 - March 4, 2021
willow park, 24 performance drive
Bennington, vermont 05201
+ Google Map
football closeup

NEFL North Atlantic Conference North Division Title holders. Home games held at Willow Park, Bennington, Vermont. What's better on a brisk fall day than packing up the family for some action packed football in a beautiful Vermont setting. Click link for season schedule and more information and their year-round schedule of games and activities.

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January 25
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
Downtown Bennington Bennington, VT 05201 United States + Google Map
glass of home brew craft beer

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 syrup pancakes

Vermont Maple Open House Weekend

March 21 - March 22

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 @ 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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July 2020

Midnight Madness – Annual Event

July 16
Downtown Bennington Bennington, VT 05201 United States + Google Map

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 Glass and the world renowned Bennington Potters go all out with their Midnight Madness celebrations.

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August 2020

Bennington Arts Weekend – Annual Event

August 1 - August 2
Downtown Bennington Bennington, VT 05201 United States + Google Map

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 Research (NCAR) for the past two years running. This collection of the highest quality arts and crafts producers gather at Camelot Village every year for one of the Best Vermont Festivals around. Food, Family fun and amazing original arts and crafts.

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Bennington Battle Day Celebration and Parade

August 16
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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September 2020

Garlic and Herb Festival – Annual Labor Day Weekend Event

September 5 - September 6
Camelot Village, 66 Colgate Heights
Bennington, VT 05201 United States
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bennington vermont event garlic festival crowds

Holy Garlic! This Southern Vermont Festival keeps getting better and better. And, now Bennington's Garlic and Herb Festival will celebrate its 25th year. Garlic ice cream, garlic goodies, and other local delicacies to eat on site and to take home. And, some of the best artisan vendors in the Northeast. This event is full to the brim with fun – Bounce houses, kiddy train, beer tents, and live music.

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Learn about more community events at the Bennington Area Chamber Calendar