Cheshire-Prospect Fall Festival

The Cheshire Fall Festival is a two-day community event on the Great Lawn at Bartlem Park, organized by the Cheshire Chamber of Commerce with the Town of Cheshire; 2026 marks its 38th year. Friday is Food Truck Friday, pairing food trucks with a Kiwanis carnival and an evening band. Saturday fills the field with roughly 80 business, nonprofit and civic booths plus a crafters row, food trucks, a farmers market and hot air balloon rides, while two stages run music, dance and martial arts through the day. The night closes with a community band set and fireworks.