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Best events in
Bennington

There's no shortage of community-focused events and things to do in Bennington, VT. The town's creative energy is fueled by local artisans and producers, with a calendar full of festivals celebrating everything from crafts to garlic. Evenings in the walkable downtown area often involve hopping between a craft brewery and a live performance.

Start an evening in the downtown district with dinner and a craft beer at Madison Brewing Company or 421 Craft Bar and Kitchen before catching a show at the Bennington Theater.
Experience the local arts scene through annual events like MayFest and ArtsFest, which fill the downtown area with artists, craft vendors, and performers.
Find community-centric events like the weekly Bennington Farmers' Market, which features live music, or trivia nights at Kelli's Tavern.

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Geneva Lewis, violin; Emma Wernig, viola; Jay Campbell, cello primary image

Geneva Lewis, violin; Emma Wernig, viola; Jay Campbell, cello

Sunday • 2:00 PM

The Campus at Marlboro Music - Ragle Hall, Serkin Center

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Cooper Foundation Fundraiser and Awards Dinner primary image

Cooper Foundation Fundraiser and Awards Dinner

Sat, Nov 7 • 5:30 PM

70 Spyglass Ln

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Round the Regions Western Mass primary image

Round the Regions Western Mass

Tue, Nov 10 • 5:00 PM

Casita

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Date Night - Taught by Madalyn primary image

Date Night - Taught by Madalyn

Fri, Nov 20 • 6:00 PM

Vermont Arts Exchange

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

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

Sat, Nov 28 • 7:00 PM

Bennington Elks Lodge #567

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The Last Waltz at the UNIHOG primary image

The Last Waltz at the UNIHOG

Sat, Nov 28 • 7:00 PM

unihog

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❄️ WINTER WONDERLAND PAINT & SIP AT KELLI’S TAVERN primary image

❄️ WINTER WONDERLAND PAINT & SIP AT KELLI’S TAVERN

Sun, Nov 29 • 3:00 PM

Kelli’s tavern

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Dec 4-6 Mount Snow $299 (2 Nights + Transport) Depart QNS NYC NJ primary image

Dec 4-6 Mount Snow $299 (2 Nights + Transport) Depart QNS NYC NJ

Fri, Dec 4 • 4:00 PM

Mount Snow Resort

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Geneva Lewis, violin; Emma Wernig, viola; Jay Campbell, cello primary image

Geneva Lewis, violin; Emma Wernig, viola; Jay Campbell, cello

Sunday • 2:00 PM

The Campus at Marlboro Music - Ragle Hall, Serkin Center

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Cooper Foundation Fundraiser and Awards Dinner primary image

Cooper Foundation Fundraiser and Awards Dinner

Sat, Nov 7 • 5:30 PM

70 Spyglass Ln

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Round the Regions Western Mass primary image

Round the Regions Western Mass

Tue, Nov 10 • 5:00 PM

Casita

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Date Night - Taught by Madalyn primary image

Date Night - Taught by Madalyn

Fri, Nov 20 • 6:00 PM

Vermont Arts Exchange

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

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

Sat, Nov 28 • 7:00 PM

Bennington Elks Lodge #567

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The Last Waltz at the UNIHOG primary image

The Last Waltz at the UNIHOG

Sat, Nov 28 • 7:00 PM

unihog

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❄️ WINTER WONDERLAND PAINT & SIP AT KELLI’S TAVERN primary image

❄️ WINTER WONDERLAND PAINT & SIP AT KELLI’S TAVERN

Sun, Nov 29 • 3:00 PM

Kelli’s tavern

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Dec 4-6 Mount Snow $299 (2 Nights + Transport) Depart QNS NYC NJ primary image

Dec 4-6 Mount Snow $299 (2 Nights + Transport) Depart QNS NYC NJ

Fri, Dec 4 • 4:00 PM

Mount Snow Resort

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SAMHAIN SÉANCE: Ancestral Collaboration with Pam Grossman & Janaka Stucky

Sunday • 6:00 PM EST

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Humanitarian Water Engineering Fall 2026

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No Title, No Permission, No Problem: Harnessing the Power of Influence

Thu, Nov 5 • 1:00 PM GMT

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Thu, Nov 12 • 2:00 PM UTC

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The Walrus Talks at Home: Canada After America

Thu, Nov 12 • 7:00 PM EST

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REVISED Cottage Food Safety Statewide Online Training

Fri, Nov 13 • 9:00 AM MST

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Fri, Nov 27 • 2:00 PM GMT

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Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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SAMHAIN SÉANCE: Ancestral Collaboration with Pam Grossman & Janaka Stucky primary image

SAMHAIN SÉANCE: Ancestral Collaboration with Pam Grossman & Janaka Stucky

Sunday • 6:00 PM EST

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Humanitarian Water Engineering Fall 2026 primary image

Humanitarian Water Engineering Fall 2026

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No Title, No Permission, No Problem: Harnessing the Power of Influence primary image

No Title, No Permission, No Problem: Harnessing the Power of Influence

Thu, Nov 5 • 1:00 PM GMT

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Lean Global Connection 2026 primary image

Lean Global Connection 2026

Thu, Nov 12 • 2:00 PM UTC

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The Walrus Talks at Home: Canada After America primary image

The Walrus Talks at Home: Canada After America

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REVISED Cottage Food Safety Statewide Online Training primary image

REVISED Cottage Food Safety Statewide Online Training

Fri, Nov 13 • 9:00 AM MST

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The MI5 Archive: Official Secrets primary image

The MI5 Archive: Official Secrets

Fri, Nov 27 • 2:00 PM GMT

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Washington Crossing the Delaware / The Crossing - Film History Livestream primary image

Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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Frequently asked questions about Bennington

Where can I find live music events in Bennington, VT?

Downtown Bennington offers several spots for live music. Bennington Theater hosts national touring acts, while places like 421 Craft Bar and Kitchen feature local performers. The Bennington Museum also has a free 'Concerts in the Courtyard' series each summer.

What are some popular outdoor events in Bennington?

The town hosts several major outdoor festivals annually. MayFest, Harvest Fest, and Garlic Town, USA! fill the streets with vendors and music. Another popular series is the Hemmings Cruise-Ins, which combine classic cars with live entertainment.

Are there free things to do in Bennington?

Yes, many community events in Bennington are free to attend. The Bennington Museum's summer concert series is a popular free event. Exploring the vendors and live music at the weekly Bennington Farmers' Market is another activity that doesn't require a ticket.

What is the nightlife like in downtown Bennington?

Bennington's nightlife centers on its downtown pubs and theater. Evenings often involve enjoying craft beer at Madison Brewing Company or catching a comedy show at Bennington Theater. Kelli's Tavern also hosts community events like trivia nights.

How can I experience the local art scene in Bennington?

Bennington's art scene is very accessible through its public events. The annual ArtsFest on the Riverwalk celebrates local artists with performances and activities. The Bennington Museum also hosts art and history exhibits alongside its concerts.

What are some family-friendly events in Bennington?

The Bennington Farmers' Market is a great family outing. Held weekly, it features local food, artisan crafts, and live music. Many of the town's annual festivals, like Harvest Fest and ArtsFest, also offer activities for all ages.

Where's the best place to see a comedy show in Bennington?

Bennington Theater is the main venue for stand-up and improv comedy. The theater brings in national touring comedians and also hosts regular improv nights, making it the go-to spot for comedy events in town.

What kinds of food and drink events happen in Bennington?

Food is central to many Bennington gatherings. The annual Garlic Town, USA! festival is a major food event, and Madison Brewing Company is a popular spot for craft beer fans. The weekly Bennington Farmers' Market also showcases local producers and food vendors.