Skip To Content

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

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

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

Bennington Battle Day Celebration and Parade

Monument Circle Old Bennington

Due to the COVID-19 pandemic, many of the traditional events that mark this celebration, such as the parade, have been cancelled in 2020. However, please stay tuned for information about

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


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

Bennington Pride Parade

The annual Bennington Pride Parade culminates a week of special events and celebration of LGBTQ+ Pride 2021!  

Learn about more community events at the Bennington Area Chamber Calendar