Downtown Annual Events | Better Bennington Corporation

Hemmings Cruise-Ins & Thursday Night Live

When: Thursdays, May- September, normally every third Thursday of the month. Click Learn More for this year's schedule
Where: Downtown Bennington (Main Street)
What: Classic and vintage cars line Main Street alongside live music as Main St closes for a lively, all-ages summer evening series.

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MayFest: Arts & Crafts Festival

When: Since 1988, MayFest takes place on in late May (last Saturday in May)
Where: Downtown Bennington (Main and School Streets)
What: A celebration of spring featuring local artists, craft vendors, live music, and community energy.

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ArtsFest

When: Last Saturday in July.
Where: Downtown Bennington Riverwalk
What: The region's art institutions, makers, and artists set up "Art Houses" to celebrate the opening reception of Sculptures at the Riverwalk with hands-on activities and entertainment.

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Harvest Fest

When: Late October (third Saturday in October)
Where: Downtown Bennington (Main and School Streets)
What: A fall celebration featuring food, games, and community activities set against Vermont’s peak foliage.

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Small Business Saturday

When: Late November (last Saturday in November)
Where: Throughout Downtown Bennington
What: A holiday shopping celebration supporting local businesses with cocoa, Santa visits, carriage rides, decorations, and special deals.

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Hemmings Cruise-Ins & Thursday Night Live

MayFest: Arts & Crafts Festival

ArtsFest

Harvest Fest

Small Business Saturday

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