MayFest

MayFest is Downtown Bennington’s cherished annual arts, crafts, music, and community festival, traditionally held on the Saturday of Memorial Day weekend. This free, family-friendly event transforms Main Street into a vibrant celebration of creativity and local culture, with handcrafted goods, live entertainment, tasty food, and activities for all ages.

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Main Street comes alive with more than 130 hand-selected vendors offering handmade jewelry, pottery, clothing, woodwork, specialty foods, and unique one-of-a-kind gifts. Beyond browsing and shopping, the festival features multiple live music stages, a dedicated Kids’ Zone, and plenty of delicious festival treats.

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39th Annual MayFest
Downtown Bennington’s Arts & Crafts Festival

Saturday, May 23, 2026, 10:00 AM – 5:00 PM

Presented by M&T Bank.

Mayfest is back, and it’s taking over downtown Bennington in the best way possible.

Main Street (Four Corners to Valentine) and School Street will close to traffic and transform into a full-day festival filled with local artists, makers, live entertainment, food, and family-friendly activities.

What to Expect

• 130+ curated arts & crafts vendors along Main Street

• 10+ food trucks on School Street

• Live music all day across two stages, sponsored by Oliver Ford of Bennington.

• Kids Zone (11 AM – 4 PM) with free activities in Merchant’s Park, sponsored by The Bank of Bennington.
   

ENTERTAINMENT

Lucky’s Stage
All Ten & John • Mister Sister • Olson Brothers • Sky Alan • Buck2Fifty

Nichols Stage
Ukulele Ensemble • Woodward Trio • Patrick Sargent • Michael Greene (BGT ’26 Winner) • Start Again

Kids Zone (Merchant’s Park | 11 AM – 4 PM) Sponsored by the Bank of Bennington

Thomson Stage Schedule

• 11:30 AM - Love Notes Choir

• 12:30 AM - The Bennington YMCA, Exercise Class

• 1:00 PM - Magic with Doug

• 2:00 PM - Dog Show

• 3:00 PM - Magic with Doug

From 11 AM - 4 PM at Merchants Park

• Art stations, yard games & interactive activities

• 501st Legion appearances & Hamster Wheel
   

Festival Details

• Free Parking: Bennington Theater, TD Bank, Town Lot

• Restrooms & Baby Changing: Mission City Church, Gamers Grotto

• Porta-potties, behind TD Bank, thanks to 802 Restrooms.

• Waste Sorting Stations: Located on School Street. Thanks to the Zero-waste committee.

• Food Trucks: School Street

• Dining Area: next to Lucky's Stage. Thanks to Lucky Dragon.

• Vendors: Main Street

• Specials by Participating Downtown Businesses

Food Trucks

Fried Dough at its Best • Tony's Concessions • Hound Dogs • 802 Soul Kitchen • Juniors Food Truck • Lemon Love • Cousins Maine Lobster • The Mac Factor / Fresh Squeezed • La Ruta Del sol • Mr. Ding-A-Ling • Polish Korner • Wild Bills Soda

This is one of Bennington’s largest and most anticipated events, and we hope to see you downtown! Scroll Down to see more details and info on this year's Hemmings Cruise-Ins!

Produced by Better Bennington Corporation.
Presented by M&T Bank

Special thanks to our valued sponsors for making Mayfest free and accessible to the community: Oliver Ford of Bennington, Bank of Bennington, Gamers Grotto, Bennington Banner, Manchester Journal, Maple Leaf Real Estate, The Coffee Bar, Mission City Church, Lucky Dragon, Len Nichols & Sons, Vista Home Improvement, LeafGuard, Stewart's Shops, The Richards Group, Casella and 802 Restrooms.

Special thanks to our volunteers!