11
October
2025
Windham's 31st Annual Autumn Affair
Celebrate the vibrant colors of fall in the Gem of the Catskills at the 31st Annual Autumn Affair, happening Columbus Day weekend, October 11 & 12, 2025, from 10 AM to 5 PM daily. This beloved Catskills tradition brings friends, neighbors, and visitors together for two days of live music, delicious food, unique shopping, and family fun.
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.
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