Apple Barn Caroling

604 US Route 7 S, Bennington, VT, United States, Vermont 05201 20 Dec 2025

A Cozy Christmas Cabaret at Bennington Theater

331 Main St, Bennington, VT, United States, Vermont 05201 20 Dec 2025

Bennington Christmas Market Extravaganza

239 Main Street, Bennington, VT, United States, Vermont 05201 20 Dec 2025

A Bennington Christmas Carol - Final Weekend

44 Gypsy Lane, Bennington, VT, United States, Vermont 05201 20 Dec 2025

Habitat Ground Breaking Ceremony #42

8 Crestwood Dr, Bennington, VT 05201-2317, United States 20 Dec 2025

Humble Pie Holiday Sale

1064 Harbour Rd, Woodford, VT 20 Dec 2025

A Bennington Christmas Carol - Final Weekend

44 Gypsy Lane, Bennington, VT, United States, Vermont 05201 21 Dec 2025

10th Annual Cabin Fever Dance – Cancer Crusaders

Elks Bennington Lodge 21 Feb 2026

2026 New Years Party w/ Start Again @ Union South

Union South VT. 3 Jan 2026

WE HONOR OUR VETERANS Dinner

American Legion Post 13 Bennington, VT 20 Dec 2025

New England Grand Family Exchange

504 Main St, Bennington, VT 05201-3039, United States 10 Jan 2026

Wine & Improv with Expert Stephanie Phelan

331 Main St, Bennington, VT, United States, Vermont 05201 18 Dec 2025

Death, Dying, Danishes (Bennington)

Bennington Community Market 19 Dec 2025

2nd Annual Ugly Sweater Party (Benefit) w/ Start Again

Union South VT. 21 Dec 2025

Pam The Berkshire Medium

American Legion Post 13 Bennington, VT 6 Feb 2026

Candle Light Service

Harvest Christian Ministries 24 Dec 2025

10th Annual Snowflake Ball

Mount Anthony-Country Club 21 Feb 2026

American Legion Riders Post 13

American Legion post 13 7 Feb 2026

PAINT & SIP

Kelli's Tavern 25 Jan 2026

NELC Spring Weekend

Elks Bennington Lodge 6 Jun 2026