Entertainment events in Bennington

Check out happening entertainment events all around Bennington, VT

Garlic Town, USA Festival 2026

 Sat, 05 Sep at 10:00 am 113 Depot St USD 6 to 33

8th Annual Downtown Bennington Food Truck Festival

 Sat, 15 Aug at 11:00 am Downtown Bennington

Blueberry Festival

 Sat, 25 Jul at 10:00 am 604 US Route 7 S, Bennington, VT

Bennington Pride 2026

 Sat, 27 Jun at 10:00 am Bennington Splash Pad & first block of Pleasant Street

SYP Summer Soirée – Presented by The Bank of Bennington

 Sat, 20 Jun at 05:00 pm Mount Anthony Country Club USD 53 to 68

LIVE COMEDY: Jonathan van Halem at Bennington Theater

 Sat, 06 Jun at 07:30 pm 331 Main St, Bennington, VT, United States, Vermont 05201

Summer Jam!

 Sat, 27 Jun at 11:00 am Willow Park

Hemmings Cruise-In (August)

 Thu, 13 Aug at 05:00 pm Main St, Bennington, VT 05201, United States

Concerts in the Courtyard: Heavy Nettles

 Fri, 26 Jun at 05:00 pm 75 West Main Street, Bennington, VT, United States, Vermont 05201

Concerts in the Courtyard: Tops of Trees

 Fri, 31 Jul at 05:00 pm 75 West Main Street, Bennington, VT, United States, Vermont 05201

Outdoor Farmers Market at Bennington Community Market

 Sat, 23 May 239 Main Street, Bennington, VT, United States, Vermont 05201

Hemmings Cruise-In (June)

 Thu, 18 Jun at 05:00 pm Main St, Bennington, VT 05201, United States

Thunderstruck: A Classic Rock Tribute

 Wed, 17 Jun at 07:30 pm Bennington Theater USD 32 to 42

Pickle Fest 🥒

Sat, 19 Sep at 10:00 am 604 US Route 7 S, Bennington, VT

Concerts in the Courtyard: Girl Blue

 Fri, 03 Jul at 05:00 pm 75 West Main Street, Bennington, VT, United States, Vermont 05201

Concerts in the Courtyard: Phil Henry and the Newsfeed

 Fri, 19 Jun at 05:00 pm 75 West Main Street, Bennington, VT, United States, Vermont 05201

Hemmings Cruise-In (July)

 Thu, 16 Jul at 05:00 pm Main St, Bennington, VT 05201, United States

Concerts in the Courtyard: Mike McMann & the Underdawgz

 Fri, 05 Jun at 05:00 pm 75 West Main Street, Bennington, VT, United States, Vermont 05201

Concerts in the Courtyard: Erin Harpe Country Blues Duo

 Fri, 07 Aug at 05:00 pm 75 West Main Street, Bennington, VT, United States, Vermont 05201

Concerts in the Courtyard: Eric Kufs & River Man

 Fri, 12 Jun at 05:00 pm 75 West Main Street, Bennington, VT, United States, Vermont 05201

Concerts in the Courtyard: Big Stone Gap

 Fri, 10 Jul at 05:00 pm 75 West Main Street, Bennington, VT, United States, Vermont 05201

Concerts in the Courtyard: Keegan James Blood

 Fri, 24 Jul at 05:00 pm 75 West Main Street, Bennington, VT, United States, Vermont 05201

Concerts in the Courtyard: The Velvet Wave

 Fri, 21 Aug at 05:00 pm 75 West Main Street, Bennington, VT, United States, Vermont 05201

Concerts in the Courtyard: Soul Porpoise

 Fri, 28 Aug at 05:00 pm 75 West Main Street, Bennington, VT, United States, Vermont 05201

Concerts in the Courtyard: The Honey Badgers

 Fri, 17 Jul at 05:00 pm 75 West Main Street, Bennington, VT, United States, Vermont 05201

Concerts in the Courtyard: SIRSY

 Fri, 14 Aug at 05:00 pm 75 West Main Street, Bennington, VT, United States, Vermont 05201

Disappearances

 Sat, 08 Aug at 07:00 pm Bennington Museum

BR&B returns to Kelli’s Tavern!

 Sat, 11 Jul at 07:00 pm Kelli's Tavern

SoberFest 2026

 Sat, 26 Sep at 11:00 am 601 Main Street, Bennington, VT, United States, Vermont 05201

IYBF! a musical comedy at Bennington Theater

 Fri, 26 Jun at 07:00 pm 331 Main St, Bennington, VT, United States, Vermont 05201