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Windham’s Annual Autumn Affair

October 9, 2021 - October 10, 2021

This year we celebrate our 26th annual Autumn Affair on Columbus Day weekend, October 9th & 10th, 2021 from 10:00 am to 5:00 pm daily. The two-day event is a popular favorite bringing friends, neighbors and visitors together to celebrate the fall season amidst the beautiful the great northern Catskills. More than fifty vendors will line both sides of Main Street with local crafts, and food in addition to the many sidewalk sales and food specials that will be offered by Main Street businesses. Live music will fill the autumn air on both days from 1 to 5pm. On Saturday, it’s local favorite, Lexy Gray and the Pioneer’s band playing on the lawn at the Centre Church, followed up on Sunday by Guilty Pleasure- a 6-piece band playing all your favorite pop songs. Kids of all ages will enjoy, Wes Laraway Wildlife Exhibit and Stunt Bike Shows and Vidbel Mountain Homestead’s Pony Rides and Petting Zoo, new this year is a Reptile Show. Stop by the Spooky Hay Maze at the Catskill Mountain Country Store, Wine & Spirit tasting at Windham Wine and Liquors for adults, Circus workshop and Kids Craft tent with pumpkin painting, Windham Mountain Resort is open for Sky rides and Mtn Bike Park, Homecoming BBQ with live music and Ski Swap Sale, Adorable Doggie Adoption booth at Coldwell Banker Village Green Realty, Live Music, Craft Beer tent and Farmers Market at The Windham Local, WRIP Remote Broadcast featuring DJ’s Jay Fink and Joe Lovero and Crazy Christine Balloons and Sean the Prankster will amaze and delight while strolling Main Street.


October 9, 2021
October 10, 2021
Event Category:


Windham Mountain
19 Resort Dr
Windham, NY 12496
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