When: Every Third Thursday, May–September 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.
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.
When: Last Saturday in June. 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.
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.
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.
