Past Events from September 24, 2022 – July 7, 2025 › Cities and Towns › Bennington › – Happy Vermont

Vermont Events

Harvest Festival in Bennington

Downtown Bennington 479 Main. Street, Bennington, VT, United States

Get ready to embrace the charm of autumn at Better Bennington Corporation's 3rd annual Harvest Fest. Enjoy live music, fall activities, food, artists, crafters, contests and prizes in the heart of downtown Bennington. The event takes place from the intersection of South and Main Streets...

Fall Festival at Whitman’s in North Bennington

Whitman's Feed Store 1873 VT Route 67 East, North Bennington, VT, United States

The third annual Fall Fest at Whitman's Feed Store in North Bennington is a free, family and pet-friendly event. Enjoy music, giveaways, a 50/50 raffle, face painting, pumpkin painting, outdoor games, food vendors and more.

Vermont’s Only Witch Trial – New England Legends in Bennington

Bennington Museum 75 Main Street, Bennington, VT, United States

Learn about Vermont's only witch trial. In the 1780s, the widow Margaret Krieger became the only person to be tried for witchcraft in Vermont. Her trial took place in the Southern Vermont town of Pownal and is documented in this soon-to-be-released episode of New England...

Snowball Bazaar in Bennington

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

Shop at the 76th Annual Snowball Bazaar in Bennington. Enjoy a Serendipity Tag sale, featuring fresh greens, desserts. pet items, crafts and gently used household goods, jewelry, books, Christmas items and more. A cafe will serve up delicious soups, breads and and dessert. A raffle...

Santa in the Stable in North Bennington

Park-McCullough Historic Governor's Mansion 1 Park Street, North Bennington, VT, United States

A holiday line-up guaranteed to provide local families a festive time in-community in the Park-McCullough Historic Governor's Mansion Carriage Barn. Visit with Santa and Mrs. Claus, enjoy cookie decorating, ornament making and other fun craft projects. The Four Corners Carolers will share holiday cheer throughout...

Winter Festival in North Bennington

Lake Paran 269 Houghton Street, North Bennington, VT, United States

The North Bennington Winter Festival includes a chili fest, sled races, baked goods, craft shows, live music and more. Find updates and a full schedule on www.facebook.com/NoBennWinterFest  

The Southern Vermont HomeBrew Festival in Bennington

Southern Vermont HomeBrew Festival 113 Depot St, Bennington, VT, United States

The Southern Vermont HomeBrew Festival in Bennington showcases over 100 different beverages to sample, a street festival vibe, food trucks, live music, vendors and more. Tickets: $30-$60 -Courtesy photo / Southern Vermont HomeBrew Festival

Opening Day at Bennington Battle Monument

Bennington Battle Monument 11 Monument Circle, Bennington, VT, United States

The Bennington Battle Monument State Historic Site opens for the 2025 season. It will be open daily through October 31. The tallest man-made building in the State of Vermont commemorates the Battle of Bennington, a pivotal victory for American forces on the New England front...

Mayfest Arts & Crafts Festival in Bennington

Downtown Bennington 479 Main. Street, Bennington, VT, United States

The 38th Mayfest Arts and Crafts Festival, an annual street fair, is one of Bennington's favorite traditions! Enjoy entertainment, food, activities, arts, crafts and more. Free admission.

Wildflower Walks in the Woods in North Bennington

Park-McCullough House 1 Park Street, North Bennington, VT, United States

Enjoy weekly walks every Tuesday morning in April and May. Rain or shine. Walk starts at the Park-McCullough veranda.

North Bennington Outdoor Sculpture Show

North Bennington Village North Bennington, United States

The 28th Annual North Bennington Outdoor Sculpture Show (NBOSS) is the longest-running outdoor sculpture exhibition in Southern Vermont. NBOSS offers local residents and visitors a unique opportunity to engage with the arts. The event's tagline says it all: "Sculptures, Hot Dogs and PBR since 1997."...

Concerts in the Courtyard at Bennington Museum

Bennington Museum 75 Main Street, Bennington, VT, United States

Spend a summer Friday evening at Bennington Museum's Concerts in the Courtyard weekly series. The museum will remain open during the concerts, which are from 5 to 7 p.m. There will be free children’s activities, and food and beverages may be purchased. Free admission. Please...