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November 2019

Oldcastle Professional Theater 2019 Season

November 1 - December 30
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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Bennington Community Theatre — 2019 Season

November 1 - December 31
$10 – $15

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.

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Southern Vermont Storm Football – 2019 – 2020 Season

November 1, 2019 - December 31, 2020
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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Bennington Musuem Events – 2019 Season

November 1 - December 30
Bennington Museum, 75 Main Street
Bennington, VT 05201 United States
+ Google Map
bennington museum things to do in bennington vermont

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.

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December 2019

Home for the Holidays Series – Annual December Events

December 1 - December 31
Downtown Bennington Bennington, VT 05201 United States + Google Map
little girls at bennington vt christmas tree lighting

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 your family this holiday season in Vermont. Come Home for the Holidays to Bennington this year. Photo by Lorianna Weathers Photography for the Bennington Area…

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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 syrup pancakes

Vermont Maple Open House Weekend

March 21, 2020 - March 22, 2020

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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July 2020

Midnight Madness – Annual Event

July 16, 2020
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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