Better Bennington Corporation's fifth annual Harvest Fest fills downtown Bennington, Vermont on Saturday, October 17, 2026, from 10 AM to 5 PM. More than 100 vendors line Main Street with handcrafted goods, fall décor, specialty foods, fresh produce and Vermont-made products, while food trucks set up on School Street. Live music runs through the day, with a Main Stage at Lucky Dragon featuring Kevin Wayne & The RetroBillies, Uken Brew, Sky Alan, Beard and Glasses and Velvet Wave. Families will find a Kid Zone in Merchants Park, and the Nichols Lot hosts historical reenactments and performances, including Bennington's Jousters. Admission is free. Vendors apply through Better Bennington's online form; all spaces are outdoors, you bring your own tent with weights and display materials, and you must be set up an hour before opening. Questions go to Better Bennington Corporation at (802) 442-5758 or info@betterbennington.com.