The Holiday Craft Market 2026

301 Park Street, Bennington, VT 7 Nov 2026

SYP Volunteer Day for Empty Bowls Bennington

Mt Anthony Union Middle School 1 Nov 2026

SYP Spiritless Speakeasy @ Left Bank

The Left Bank 29 Oct 2026

North Bennington Karaoke Night w/ SYP

Pangaea Café 20 Nov 2026

Family Day & Children's Shopping

Bennington Museum 5 Dec 2026

Bennington Bash Scavenger Hunt

The Coffee Bar 2 Sep 2024

The American Table REBROADCAST Presentation

Brookdale Fillmore Pond 6 Nov 2026

Brave Little State at The Miller's Toll

The Miller's Toll Dinner Club and Lounge 28 Oct 2026

Basket Bingo

Bennington Rural Fire Department Company #1 20 Nov 2026

PTG Sponsored Trunk or Treat

181 Orchard Rd, Bennington, VT 28 Oct 2026

Nuncrackers (The Nunsense Christmas Musical) - Bennington Community Theater 2026 Season (play 4/4)

331 Main St, Bennington, VT, United States, Vermont 05201 4 Dec 2026

Pro Wrestling returns to Bennington VT for Toys for Tots 11/28/26

Bennington Elks Lodge #567 28 Nov 2026

❄️ WINTER WONDERLAND PAINT & SIP AT KELLI’S TAVERN

Kelli’s tavern 29 Nov 2026

BECC 4th Annual Winter Craft Fair & Raffle

1506 Harwood Hill Rd, Bennington, VT, United States, Vermont 05201 21 Nov 2026

DuFour's 3rd Annual Trunk or Treat

272 Benmont Ave Bennington, VT 05201 31 Oct 2026

CHRISTMAS PAINT & SIP – CANVAS TOTE BAG WORKSHOP

Kelli's Tavern 13 Dec 2026

IMPROV AFTER 5 at Bennington Theater (Every 3rd Thursday)

331 Main St, Bennington, VT, United States, Vermont 05201 15 Oct 2026

5-Week Adult Studio Access

Vermont Arts Exchange 9 Nov 2026

Noon Year's Eve Party

Bennington Museum 31 Dec 2026

Bridges of Bennington County

Bennington Museum 15 Nov 2026