By Ahmad Yassir, Vermont Country Magazine.
Spring in Southern Vermont has a way of announcing itself in full color, trees budding along the streets, storefronts throwing open their doors, and neighbors gathering once again in the heart of downtown. In Bennington, that seasonal tradition has a name: MayFest.
On Saturday, May 23, from 10 a.m. to 5 p.m., Better Bennington Corporation (BBC) invites visitors and locals alike to the 39th annual MayFest: Downtown Bennington’s Arts & Crafts Festival, presented this year by M&T Bank. Event sponsors also include Oliver Ford of Bennington, Bank of Bennington, Gamers Grotto, LeafGuard, The Richards Group, Maple Leaf Real Estate and Vermont News and Media through the Bennington Banner and Manchester Journal.
For nearly four decades, MayFest has marked the unofficial beginning of Bennington’s event season, transforming Main Street into a vibrant celebration of craftsmanship, community and the creative spirit of the region.
This year, Main Street will be closed from Four Corners to Valentine Street, with School Street also closed from Main Street to Pleasant Street, creating a walkable festival corridor filled with shopping, music, food and family activities.
A Showcase of Regional Craftsmanship
At the heart of MayFest are 130 highly curated vendors, each selected to reflect the rich artistry and craftsmanship of our region.
Visitors can expect a diverse mix of handmade goods, from beautifully engraved woodwork and handcrafted cutting boards to ceramics, jewelry, original artwork, textiles and locally made candles. The artistry extends well beyond traditional crafts, with specialty food producers, distillers and an inviting lineup of food trucks adding to the festival experience.
It’s also one of the best days of the year to explore downtown’s brick-and-mortar businesses. Shops and restaurants throughout the district will join the celebration with sidewalk sales, extended hours, specials and promotions, welcoming the thousands of visitors who return each year for this beloved tradition.
Music All Day in the Heart of Downtown
Entertainment will run throughout the day, centered around the Main Stage at Lucky Dragon.
This year’s lineup features a strong mix of local and regional talent, beginning with All Ten & John, followed by Mister Sister, The Olson Brothers, Sky Alan, and closing out the day with headliner Buck2fifty.
All performances are free to attend, thanks to the generous support of Oliver Automotive Group.
A second performance area will also be located in the Nichols lot, bringing even more energy and movement throughout the festival footprint. Featuring The Ukulele Ensemble and Woodward Trio, Patrick Sargent, Michael Greene, and Start Again.
Family-Friendly Fun
MayFest continues to grow as a family destination, and this year’s children’s programming is especially exciting.
With support from Bank of Bennington, the Kids Zone at Merchants Park and the Splash Pad will offer free activities from 11 a.m. to 4 p.m.
Families can enjoy art-making stations, yard games, interactive experiences and two magic shows. This year’s standout surprise is sure to be a hit: a kid-sized hamster wheel that powers a frozen beverage machine, giving children the chance to create their own refreshing drink through movement and play.
It’s a playful and memorable addition to a festival already known for creating joyful moments downtown.
Thoughtful Logistics and Sustainability
Festival organizers have also made it easy for visitors to plan their day.
Parking remains free throughout Bennington, with suggested lots at TD Bank, Bennington Theater and the Town Offices lot.
Restroom access will be available in the TD Bank parking lot thanks to 802 Restrooms, while additional public bathrooms and baby changing facilities can be found at Gamers Grotto and Mission City Church.
A dedicated dining area will be located at Lucky Dragon, creating a central gathering space for festivalgoers to relax and enjoy the atmosphere.
This year also marks an important step in Better Bennington’s commitment to sustainability. In partnership with Bennington’s Zero-Waste Committee and Casella, the organization is beginning a gradual initiative toward zero-waste events.
Visitors will notice volunteers stationed throughout the festival helping sort compost and recycling, an effort that reflects Bennington’s ongoing commitment to environmental stewardship.
MayFest is more than a street festival, it’s a seasonal homecoming.
As the trees bloom and downtown comes alive, the event offers an ideal reason for day-trippers and weekend visitors to make the drive, whether from nearby Berkshire towns, across Southern Vermont, or from larger cities like Boston and New York City.
It’s a celebration of what makes Bennington special: creativity, hospitality, local business and community pride.
From the first vendor booth to the last encore, dedicated volunteers, entertainers and downtown merchants will be ready to ensure every guest enjoys the very best of Bennington.
To plan your visit and stay updated on specials, offers and event news, follow Better Bennington Corporation on social media and through its newsletter when you visit BetterBennington.com
