Windham’s 32nd Annual Autumn Affair is this weekend
Published on:
October 8, 2026
The town will be packed with live music, shopping, family activities and more than 60 craft, artisan, maker and food vendors. Photo contributed.
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WINDHAM —Windham’s biggest fall weekend is here and the town is ready to welcome residents, visitors, vendors and friends for the 32nd Annual Autumn Affair.
This weekend, October 10-11, Main Street, Centre Church, the Windham-Ashland-Jewett school campus and businesses throughout Windham will be filled with live music, great food, shopping, family activities and more than 60 craft, artisan, maker and food vendors.
On Saturday from 12–4 p.m., Lex Grey and The Urban Pioneers bring classic rock and blues to the Main Stage at Centre Church. Then on Sunday from 12–4 p.m., Steel takes over the Main Stage with R&B favorites.
But that's only the beginning. Saturday's music includes Joe Tobin from 10 a.m. to 1 p.m. at the Windham Farmers Market, The Christine Spero Group from 12–4 p.m. at Millrock Restaurant & Bar Room, The Score from 2–5 p.m. at Windham Wine & Liquors, and Dan Pitts from 7–9 p.m. at The Windham Local.
On Sunday, catch Soul Purpose, a nine-piece band, from 12–5 p.m. at The Windham Local, and Shane Rennison from 12–4 p.m. at Millrock Restaurant & Bar Room.
Mountain King Brewing Company will also feature live music and Chef Luke's Fresh Start Food Truck both days, while Taphouse & Grille joins the weekend with autumn cocktails and live music.
Saturday brings even more reasons to spend the day exploring Windham. Inside Centre Church from 11 a.m. to 1 p.m., the Autumn Affair Baking Competition welcomes bakers of all levels. Come see what our local bakers have created and cheer on your favorites.
WRIP will broadcast live from Main Street from 10 a.m. to 4 p.m., with DJs Jay Fink and Joe Loverro joining the festivities.
Over at the Methodist Church, Apple Fest runs from 10 a.m. to 4 p.m., complete with the famous apple fritters.
The Windham Farmers Market is open from 9 a.m. to 1 p.m., and Windham Mountain Club's Season Passholders Homecoming and the WAJ Ski Swap add to that unmistakable feeling that another ski season is right around the corner. The Ski Swap runs 9 a.m. to 3 p.m. on Saturday.
And keep an eye out for Mr. Pumpkin Head, the stilt walker, making his way around Main Street.
The WAJ campus will be filled with family fun Saturday and Sunday, including wildlife and reptile exhibits, kids' crafts, games and activities, axe throwing, Mike the Juggler, a sheriff's K-9 demonstration, child ID station, food, vendors and the chamber silent auction.
The Windham Hose Company will host touch-a-truck and free hot dogs, while across the street, the Vidbel Mountain Homestead Petting Zoo will be ready to introduce youngsters to some furry new friends.
For a little Halloween fun, make your way to the Spooky Hay Maze at Catskill Mountain Country Store.
And don't leave four-legged friends home. The Coldwell Banker Village Green Realty Doggie Photo Contest returns Saturday and Sunday.
Autumn Affair has grown into much more than the festival grounds. Businesses throughout Windham are getting into the spirit with food, drinks, shopping, music and special activities.
In addition to the dozens of craft, artisan, maker and food vendors throughout the festival, the Greek Church Tent will be serving authentic Greek specialties.
Stop at Main Street Market for sausage and peppers, enjoy free wine and chocolate pairing at Gem Mercantile from 10 a.m. to 1 p.m. Saturday, or visit Windham Wine & Liquors for wine and spirit tastings and live music by The Score from 2-5 p.m.
Local businesses are joining the celebration throughout Columbus Day Weekend. Wylder Windham has lodging specials and activities; Eastwind Hotel Dandies restaurant with its Biergarten; Chicken Run has weekend music; and Lilly's Steak & Cocktails and Tip Tapp Tavern are among the local businesses welcoming Autumn Affair weekend visitors.
And don't forget the Main Street sidewalk sales. Take some time to wander, shop local, grab something to eat and see what you discover along the way.
There is no admission fee and free parking can be found at Creamery Pond and Windham Mountain Club Lower Parking Lot. Portable restrooms will be available at the WAJ campus and by the handicap ramp next to the Windham Library.
For event information and updates, visit MovingWindhamForward.com.
