Vermont Fairs, Festivals & Art Shows
Music Festivals 2026–2027
Cities / Towns
Bennington Bristol Milton Quechee Rutland Woodstock

Music Festivals 2026–2027

Vermont Cities and Towns

Bennington, Bristol, Milton, Quechee, Rutland, Woodstock

Attend Your Favorite Music Festivals in Vermont

 
Woodstock Art Festival
September 12 - 13, 2026

Woodstock Art Festival

Woodstock Village Green, Woodstock, VT

Status: Updated 8/20/2026

An Art Show organized by Woodstock Area Chamber of Commerce.
This Vermont Art Show will have fine art exhibitors and no food booths. There will be Roving Performers with Local talent and the hours will be Sat 10am-5pm; Sun 10am-4pm.
Art & Stroll
September 19, 2026

Art & Stroll

199 US-7 South, Milton, VT

Status: Updated 8/28/2026

A Craft Show organized by Milton Artist's Guild.
This Vermont Craft Show will have antique/collectibles, crafts, fine art and fine craft exhibitors, and 3 food booths. There will be 1 stage with Regional and Local talent and the hours will be Sat 10am-4pm.
Bristol Harvest Festival
September 26, 2026

Bristol Harvest Festival

Bristol Town Green, Bristol, VT

Status: Updated 7/22/2026

A Family & Kids Festival organized by Addison County Chamber of Commerce.
This Vermont Family & Kids Festival will have crafts exhibitors and no food booths. There will be 1 stage with Local talent and the hours will be Sat 10am-3pm.
Art in the Park Fall Foliage Festival
October 10 - 11, 2026

Art in the Park Fall Foliage Festival

Main Street Park, Rutland, VT

Status: Updated 5/14/2026

A Craft Show organized by Chaffee Art Center.
This Vermont Craft Show will have fine art, fine craft and homegrown products exhibitors, and 4 food booths. There will be 1 stage with Regional and Local talent and the hours will be Sat 10am-5pm; Sun 10am-4pm. This event will also include: children's activity area, demonstrations.
Harvest Fest
October 17, 2026

Harvest Fest

Downtown, Bennington, VT

Status: Updated 1/19/2026

A Family & Kids Festival organized by Better Bennington Corporation.
This Vermont Family & Kids Festival will have antique/collectibles, commercial/retail, corp./information, crafts, fine art, fine craft and homegrown products exhibitors, and 15 food booths. There will be 2 stages with Regional and Local talent and the hours will be Sat 10am-5pm. This event will also include: face painting, hair braiding, kids' games, pumpkin painting, story telling.
 
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