Windham Chamber Autumn Affair
October 10 @ 1:00 PM - 4:00 PM
Saturday Oct 10: Lex Grey and the Urban Pioneers at the 2026 Windham Autumn Affair!
This beloved Catskills tradition brings friends, neighbors, and visitors together for two days of live music, delicious food, unique shopping, and family fun!
- Location: Main Street, Windham, NY 12496
- Bandstand: Corner of Church & Main
- The 32nd Annual Autumn Affair in Windham, NY will take place Columbus Day Weekend, Sat & Sunday Oct 10 and 11 2026 from 10:00 AM to 5:00 PM daily.
- Main Street will come alive with more than 50 vendors offering local crafts, seasonal treats, and specialty foods, plus sidewalk sales from Windham’s Main Street businesses. Festival highlights include hay wagon rides, axe throwing, chainsaw carving demonstrations, and kid-friendly entertainment
- Free parking is available at Windham Mountain Club and throughout town, and admission is free so bring the family, explore the festivities, and enjoy the beauty of autumn in the Great Northern Catskills.