Bennington MayFest (39th Annual Arts & Crafts Festival)

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. 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. 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 artis...