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North Bennington Halloween Parade

Vermont Arts Exchange 48 Main Street, North Bennington, VT

Join us for another annual wild and weirdly fun walk down Main Street and back to Lion's Park. Costume Awards, Bonfire, and more! Lift off from Vermont Arts Exchange (VAE - next to No. Bennington Post Office).

Bread & Puppet Theater

Monument Arts & Cultural Center 44 Gypsy Lane, Bennington, VT, United States

From the Bread and Puppet website: Inflammatory Earthling Rants with Help from Kropotkin will tour again! Earthlings are now aflame and consequently need inflammatory rants, directed against the arsonist: Western Civilization and its incompetent government. The habitual pragmatic communication jargon won’t do, so the ranters have to resort to the original language which was tasked to

Sage City Symphony

VAPA/Greenwall Auditorium - Bennington College 1 College Drive, Bennington, VT, United States

Felix Mendelssohn: Symphony #5 "The Reformation"; Maurice Ravel: Mother Goose Suite; Wolfgang Amadeus Mozart: Overture to The Magic Flute; Works by Bennington College Students: Understory, TBD SPONSORED BY M&T Bank

Small Business Saturday 2023

Bennington, VT - Various Locations Bennington

Small Business Saturday is a great day to kick off the holiday shopping season while supporting your favorite small businesses that make our community unique. This annual national shopping day has been going strong since 2010 and occurs the first Saturday after Thanksgiving. Bennington will be celebrating Small Business Saturday with special events and deals

Bennington Theater – Jon Rudnitsky Performance

Bennington Theater 331 Main Street, Bennington, VT, United States

Jon Rudnitsky was the only new castmember hired for the 41st season of SNL, and Young Larry on the latest season of CURB YOUR ENTHUSIASM. He has appeared in leading roles opposite Reese Witherspoon in the Nancy Meyers film HOME AGAIN, alongside George Clooney in the Hulu mini series CATCH 22, the Netflix movie SET

75th Annual Snowball Bazaar – Second Congregational Church, UCC

Second Congregational Church 115 Hillside Avenue, Bennington, VT, United States

Come and experience the famous Bazaar while shopping our selection of beautiful, fresh greens, delicious baked goods, pet items, crafts, and the  Serendipity sale - 4 large rooms packed with gently used items: kitchen items, books, jewelry, tools, household goods, Christmas items, toys, and more. The Snowball Cafe will feature delicious homemade soups and desserts. 

A Festive Gathering: Embracing Unity This Holiday Season

Merchant's Park Thomson Family Stage 119 North Street, Bennington, Vermont

The BBC welcomes all to a festive holiday gathering at the Thomson Stage at Merchants Park featuring: The Four Corner Carolers (3pm performance) A Visit From Santa Claus Christmas Tree Lighting Menorah Lighting Hot Cocoa Bar & Treats And Maybe Another Surprise or Two!   Sponsored by: Heritage Family Credit Union, Different Strokes Paint, Home

Kat Wright & Brett Hughes 2023 Holiday Show

The Coffee Bar 109 South Street, Bennington, Vermont

Kat Wright & Brett Hughes, two of Vermont’s most beloved songbirds, join forces once again for their 10th annual VT holiday tour. The show - a true Christmas gift offers songs of holiday heartbreak & holiday cheer - bejeweled with storytelling, originals, and beloved classics alike. It’s guaranteed to warm your heart, peak your nostalgia

Holiday Craft Fair

First Baptist Church 601 Main Street, Bennington, VT, United States

The annual Holiday Craft Fair hosted by the Developmental Services Connections program returns on December 8, 2023, at the First Baptist Church in Bennington, VT. Clients of UCS’ Developmental Services division will host the event, and other local crafters, artists, and makers in the community are invited to attend as vendors. Shoppers can stop by

Learn about more community events at the Bennington Area Chamber Calendar