Cummington Fair 2026 — Aug 27–30 in Cummington, MA

The Cummington Fair on August 27-30, 2026, is a four-day agricultural fair in the western Massachusetts hilltowns, held at the historic Cummington Fairgrounds. Founded in 1883 and run by the Hillside Agricultural Society, the fair features livestock and agricultural exhibits, horse pulls, ox pulls, vintage tractor displays, a midway with rides, food vendors, craft vendors, live entertainment, and traditional country fair competitions. It is the largest annual gathering in the Hampshire County hilltowns.