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Festivals in Bennington, VT.
Festivals, Family & Kids Festivals

Featured Events

May 24, 2025

betterbennington.com/event-details/mayfest-..

(802) 442-5758
Beautiful Downtown - Bennington, VT

Mayfest is an arts & crafts fair in its 38th year that features over 120 craft and food vendors and consistently attracts over 10,000 attendees annually. 2024 was a sold-out show! We've added a great kids zone full of free activities! Come enjoy a day of fine crafts, food, family entertainment, and beautiful spring in Southern Vermont!

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Events in Bennington, VT — upcoming

Maple in April at the Barn
April 2025 (dates not updated)

Maple in April at the Barn

The Apple Barn and Bakeshop, Bennington, VT

Status: Updated 2/17/2024

A Festival organized by The Apple Barn and Bakeshop With Orchard Air LLC.
This Vermont Festival will have crafts, fine art, fine craft and homegrown products exhibitors, and 7 food booths. There will be 1 stage with Local talent and the hours will be Sat 10am-6pm. This event will also include: demonstrations, kids' area, live music.
Roots & Blooms Festival - Celebrating Spring and Moms
May 2025 (dates not updated)

Roots & Blooms Festival - Celebrating Spring and Moms

The Apple Barn and Bakeshop Field, Bennington, VT

Status: Updated 2/17/2024

A Festival organized by The Apple Barn and Bakeshop With Orchard Air LLC.
This Vermont Festival will have antique/collectibles, crafts, fine art, fine craft, flea market and homegrown products exhibitors, and 5 food booths. There will be 1 stage with Regional and Local talent and the hours will be Sat 10am-6pm. This event will also include: chair massages, photo booth, signature cocktails, kids area, entertainment, activites.
Flavors of Vermont: Food Festival at the Barn
June 2025 (dates not updated)

Flavors of Vermont: Food Festival at the Barn

The Apple Barn Field, Bennington, VT

Status: Updated 2/17/2024

A Food Festival organized by The Apple Barn and Bakeshop With Orchard Air LLC.
This Vermont Food Festival will have homegrown products exhibitors and 8 food booths. There will be 1 stage with Regional and Local talent and the hours will be Sat 10am-6pm. This event will also include: live music, activities, contests, demonstrations, kids area.
Blueberry Festival at the Barn
July 2025 (dates not updated)

Blueberry Festival at the Barn

The Apple Barn and Country Bake Shop, Bennington, VT

Status: Updated 2/17/2024

A Festival organized by The Apple Barn and Bakeshop With Orchard Air LLC.
This Vermont Festival will have antique/collectibles, commercial/retail, crafts, fine art, fine craft, flea market and homegrown products exhibitors, and 5 food booths. There will be 1 stage with Regional and Local talent and the hours will be Sat 10am-6pm. This event will also include: blueberry picking, games, contests, activities, live music.
Bennington Food Truck Festival
August 2025 (dates not updated)

Bennington Food Truck Festival

Downtown, Bennington, VT

Status: Updated 2/13/2024

A Food Festival organized by Green Mountain Concessions.
This Vermont Food Festival will have crafts, film, fine art, fine craft and homegrown products exhibitors, and 20 food booths. There will be 1 stage with Local talent and the hours will be Sat 11am-7pm. This event will also include other activities such as face-painting and ax throwing booth.
Clothing Extravaganza at the Barn
August 2025 (dates not updated)

Clothing Extravaganza at the Barn

The Apple Barn and Bakeshop Field, Bennington, VT

Status: Updated 2/17/2024

A Festival organized by The Apple Barn and Bakeshop With Orchard Air LLC.
This Vermont Festival will have flea market exhibitors and no food booths. This event will also include kids area.
Bennigton Vermont Garlic & Herb Festival
August 2025 (dates not updated)

Bennigton Vermont Garlic & Herb Festival

Downtown, Bennington, VT

Status: Updated 2/22/2024

A Specialty-Theme Event organized by Bennington Area Chamber of Commerce.
This Vermont Specialty-Theme Event will have crafts and homegrown products exhibitors, and tba food booths. There will be 2 stages with Regional and Local talent and the hours will be Sat 10am-5pm. Admission tickets are $5 - $30. This event will also include: demos, lectures, face painting, kids activity tent.
Heritage Harvest Festival at the Barn
September 2025 (dates not updated)

Heritage Harvest Festival at the Barn

The Apple Barn and Bakeshop Field, Bennington, VT

Status: Updated 2/17/2024

A Festival organized by The Apple Barn and Bakeshop With Orchard Air LLC.
This Vermont Festival will have antique/collectibles, commercial/retail, crafts, fine art, fine craft, flea market and homegrown products exhibitors, and 5 food booths. There will be 1 stage with Regional and Local talent and the hours will be Sat 10am-6pm. This event will also include: eating contests, corn maze, childrens' activities, bar, live music, activities.
Harvest Fest
October 2025 (dates not updated)

Harvest Fest

Downtown, Bennington, VT

Status: Updated 8/13/2024

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 25 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, fall themed contest, etc.
Spirits of Samhain Festival - Halloween and Samhain
October 2025 (dates not updated)

Spirits of Samhain Festival - Halloween and Samhain

The Apple Barn and Bakeshop Field, Bennington, VT

Status: Updated 2/17/2024

A Festival organized by The Apple Barn and Bakeshop With Orchard Air LLC.
This Vermont Festival will have antique/collectibles, commercial/retail, crafts, film, fine art, fine craft, flea market and homegrown products exhibitors, and 5 food booths. There will be 1 stage with Regional and Local talent and the hours will be Sat 3pm-9pm. This event will also include: live music, demonstrations, games, contests, activities, spookiness, fairies.