Bennington’s Mayfest Celebrates its 38th Year

By Gabriel Schatz, Vermont Country Magazine.

In a state where winter lasts half the year, spring demands to be celebrated with extra gusto. And no one is more excited for the return of warm weather than Vermonters. Every Memorial Day weekend, downtown Bennington bursts to life as it hosts the beloved annual Mayfest Arts & Crafts Festival. Now celebrating its 38th year, this spring tradition transforms Main Street into a bustling celebration of arts, music, food, and entertainment. On Saturday, May 24, 2025, Mayfest invites residents and visitors alike to celebrate renewal and the returning of the light in the best way we know how—with good food, live tunes, big crowds, and abundant smiles.

Walking down Main Street during Mayfest means stepping into a whirl of color and creativity. Stretching from one end of the street to the other, the festival showcases an impressive array of local and regional artisans. This year’s event will feature more than 130 vendors lining Main Street and School Street, each hand-selected for producing their own handmade, homemade, designed, or homegrown products. From beautifully crafted pottery and intricate jewelry to handmade clothing, woodworking, and unique home décor, every booth holds a treasure waiting to be found.

Some standout vendors include Oat’s Barkery (handmade dog treats), Chef Tim Foods (specialty gourmet goods), Vermont Wildlife (nature-themed art and décor), Golden Leaf Designs (jewelry), Ardent Flame (candles and aromatherapy), and Serenity Bamboo Flutes (handcrafted instruments). 

But the festival’s charm isn’t limited to arts and crafts alone. Mayfest offers a treat for the taste buds, with food vendors serving everything from classic festival snacks like fried dough and lemonade to fried cheese curds, BBQ, and even Jamaican cuisine. New food trucks will also join the festival this year, dishing up fresh local flavors and festival favorites. Whether you’re craving savory comfort food or sweet indulgences, you’ll have plenty of options to choose from.

The three live event stages at Mayfest keep festival-goers entertained between bites and browsing. This year’s musical lineup includes Hidden Angel Records, All Ten & John, Cosby Gibson & Tom Staudle, J2, The Ukulele String Ensemble, and The Woodwind Trio, with even more acts to be announced soon. Expect everything from acoustic folk to energetic covers to fill the streets with rhythm and joy.

Beyond music and shows, children and families will find endless fun in the dedicated Kid’s Zone. New this year is a petting zoo from New England Party Animals, where kids can meet bunnies, hamsters, guinea pigs, ducklings, chickens, goats, and lambs. (Please note: personal pets are not allowed in this area for the safety of the animals and attendees.) The Kid’s Zone will also feature interactive games, face painting, crafts, and activities that guarantee smiles all around.

The heart of Mayfest lies in its ability to capture the essence of Southern Vermont, a region defined by its commitment to community. Neighbors meet neighbors, friends reconnect after long winters, and visitors quickly feel at home amid the friendly faces and festive atmosphere. The sense of community pride shines brightly as people gather to support local creators, small businesses, and performers, emphasizing what makes Bennington such a special place.

As Jeanne Mintrone, Executive Director of the Better Bennington Corporation, proudly notes, Mayfest brings “big-city festival excitement” to the Green Mountain State. “Every vendor is hand-selected,” she says, “which makes this event a perfect opportunity to support small businesses directly.” 

Keith Carey, president of the BBC Board of Directors, adds: “It’s an incredible day to experience Bennington — to shop local, eat local, and enjoy local talent.” 

There’s no need for extensive travel or complicated plans—just stroll down Main Street for a day filled with art, music, food, family, and fun. Join the celebration on May 24 and experience firsthand the joy, creativity, and community pride that makes Mayfest a beloved Southern Vermont tradition.

Free parking is available throughout downtown, including lots at TD Bank, behind the Town Offices, near the Bennington Theater, and along Union Street.

For updates, full schedules, and more, visit betterbennington.com or follow the Better Bennington Corporation on social media.

Gabriel Schatz is a Bennington local who enjoys getting lost in the woods with his two black labs. When Gabriel isn’t exploring the wilder parts of the Green Mountains, he can usually be found in the kitchen where he enjoys cooking Mexican and South Asian cuisine, or on the couch starting an epic fantasy novel that he will inevitably give up halfway through in favor of yet another Terry Pratchett book.