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Holiday events
in Bennington, VT

Discover the best Holiday events in your area and online

Holiday
Bennington
Date
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Most popular events

Ramble Around Town: Hayride Bar Crawl 2026 primary image

Ramble Around Town: Hayride Bar Crawl 2026

Sun, Oct 11, 2:00 PM

American Legion

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Cricket Creek Fall Farm Picnic primary image

Cricket Creek Fall Farm Picnic

Sat, Oct 24, 11:00 AM + 1 more

Cricket Creek Farm

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Santa Express 2026 primary image

Santa Express 2026

Sat, Dec 12, 10:00 AM + 4 more

r.k. Miles Depot Station

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Santa Express Evening Train primary image

Santa Express Evening Train

Fri, Dec 11, 7:00 PM

r.k. Miles Depot Station

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Halloweirdo Night primary image

Halloweirdo Night

Thu, Oct 15, 7:00 PM

No Fun

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Pumpkin Carving at Troy Rewind Oct 20 2026 primary image

Pumpkin Carving at Troy Rewind Oct 20 2026

Tue, Oct 20, 7:00 PM

Troy Rewind

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NEW YEAR'S EVE primary image

NEW YEAR'S EVE

Thu, Dec 31, 6:00 PM

Proprietor's Lodge

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BRING IN 2027 AT THE VENUE primary image

BRING IN 2027 AT THE VENUE

Thu, Dec 31, 6:00 PM

The Venue At Skyline

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