Things To Do Annual Events
From winter celebrations to summer festivals and fall traditions, Bennington’s annual events showcase the town’s vibrant arts scene, deep history, outdoor culture, and strong sense of community. Throughout the year, festivals, markets, performances, and family-friendly gatherings invite visitors to experience Bennington, Vermont through its local traditions, creative energy, and signature celebrations.
Signature Annual Events
Winterfest in North Bennington
When: January (second to last Saturday in January)
Where: North Bennington
What: A free family-friendly, four hours winter celebration featuring live music, craft vendors, food, and seasonal fun—proof that Vermonters embrace winter at its coldest.
Southern Vermont HomeBrew Festival
When: Early May (first Saturday in May)
Where: Downtown Bennington
What: A popular early-summer festival bringing together homebrewers from Vermont and the Capital Region for tastings, food trucks, live entertainment, and audience voting.
Hemmings Cruise-Ins & Thursday Night Live
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.
Mayfest: Arts & Crafts Festival
When: Late May (last Saturday in May)
Where: Downtown Bennington
What: A celebration of spring featuring local artists, craft vendors, live music, and community energy.
Downtown Bennington Food Truck Festival
When: Mid-August
Where: Downtown Bennington
What: A favorite summer event showcasing diverse food trucks, live music, and a beer tent in the heart of downtown.
North Bennington Outdoor Sculpture Show (NBOSS)
48 Main Street
North Bennington, VT
When: Late June (last Saturday in June)
Where: North Bennington
What: Since 1997, the annual outdoor sculpture show features more than 50 works, live music, free food, and interactive activities.
Bennington Battle Day Weekend
When: Weekend closest to August 16
Where: Various locations throughout Bennington
What: Vermont’s state holiday commemorating the 1777 Battle of Bennington with reenactments, educational programming, and family-friendly events.
Garlic Town, USA!
When: Labor Day Weekend
Where: Downtown Bennington
What: Bennington’s signature garlic festival, featuring hundreds of vendors, live music, food, family activities, and festive fun for all ages.
TrailFest
When: Late July (last Saturday in July)
Where: Bennington Recreation Center
What: A free community event celebrating Bennington’s trail networks and outdoor recreation culture, welcoming hikers, locals, and visitors alike.
Bennington’s Trunk or Treat
When: Late October (last Saturday in October)
Where: Coggins Auto Group
What: A safe, family-friendly Halloween celebration featuring decorated trunks, food trucks, entertainment, and costumes for thousands of participants.
Quilt Fest
When: Second week of September
Where: Mount Anthony Union Middle School
What: A celebration of quilting and textile art, featuring vibrant displays, artists, and New England craft traditions.
Stone Skipping at Lake Paran
When: Late September
Where: Lake Paran, North Bennington
What: A beloved annual gathering where families and friends come together for friendly competition and lakeside fun.
Harvest Fest
When: Late October (third Saturday in October)
Where: Downtown Bennington
What: A fall celebration featuring food, games, and community activities set against Vermont’s peak foliage.
Small Business Saturday
When: Late November (last Saturday in November)
Where: Throughout Bennington
What: A holiday shopping celebration supporting local businesses with cocoa, Santa visits, carriage rides, decorations, and special deals.
Year-Round Arts, Culture, and Entertainment
Bennington’s year-round arts, culture, and entertainment organizations offer a steady calendar of events, performances, exhibitions, and educational programming. From theaters and galleries to music venues and cultural centers, these organizations help make Bennington, Vermont a creative destination in every season.
Bennington Museum
75 Main Street,
Bennington, Vermont
Largest collection of Grandma Moses art and memorabilia available to the public. Fine collections of paintings, pottery, fine furniture, and historical objects that evoke the rich heritage of Vermont.
Bennington Theater
331 Main Street
Bennington, Vermont 05201
Check out this ‘great little gem’ of a professional theatre, featuring amazing productions in an intimate performance space. Plus, national touring comedians, musicians, and community events.
Monument Arts & Cultural Center
44 Gypsy Lane
Bennington, VT 05201
The Monument Arts & Cultural Center is a unique and inviting home for theater, concerts, artist exhibits, outdoor music, workshops, dance classes, art classes, and so much more.
Vermont Arts Exchange (VAE)
48 Main Street
North Bennington, VT 05257
VAE is a nonprofit community arts organization with a mission to strengthen communities and neighborhoods through the arts. VAE produces a variety of programs and events, including the Basement Concert Series, exhibitions, and summer camps.