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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

Bennington Arts Weekend – Annual Event

Downtown Bennington Bennington

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

Oldcastle Professional Theater 2020 Season

Downtown Bennington Bennington

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!

Bennington Battle Day Celebration and Parade

Monument Circle Old Bennington

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,

Garlic and Herb Festival – Annual Labor Day Weekend Event

Camelot Village 66 Colgate Heights, Bennington

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

Quiltfest – Annual Event

Mount Anthony Union Middle School 747 East Road, Bennington

There’s a reason this show has been around for 26 years! Come for an action-packed weekend of education, challenge quilts, demonstrations and comradery in the beautiful green mountain state.

Food Truck Festival – Annual Event

Downtown Bennington Bennington

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

Southern Vermont Fall HomeBrew Festival

Previously known as the Summer HomeBrew Festival, this has been postponed to the fall (assuming it's deemed safe to hold it at that time; the organizers plan to implement many safety precautions). This festival will be held at the old Tuttle's lot behind the Bennington Brush Building. There will be plenty of excellent food, live

Winterfest

Lake Paran Houghton Lane, North Bennington

  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.

Southern Vermont Storm Football – 2020 Season

willow park 24 performance drive, Bennington

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.

Learn about more community events at the Bennington Area Chamber Calendar