Chatham WinterFest 2024 in Chatham, NY

Kick off your holiday in Chatham and enjoy festive local shopping, food and drinks. Santa, carolers, music, gift basket raffle, cookie contest and more!

Dozens of independent retail shops. You’ll find something for everyone on your list.
Dozens of options for food and drink. Indulge all your festive cravings.

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Events & Activities

11:00am-12:30pm Visit from Santa Claus at Stone House Properties, 6 Main Street

Noon Cooking Baking Contest judging at Red Mannequin in the Clocktower building

12:30am-1:00pm Visit from Santa Claus at Morris Memorial, 17 Park Row

1:00pm Free showing of the movie Elf at Morris Memorial, 17 Park Row

1:00-5:00pm Wine & Cheese tasting at Chatham Wine & Liquor, 53 Main Street

11:00am-4:00pm Klocke Estate Vermouth Tasting at Park Row Gallery, 57 Main Street

11:00am-4:00pm HandCrafters Too PopUp showing local artisans at Park Row Gallery, 57 Main Street

3:00pm Chatham Children’s Chorus performance at Morris Memorial, 17 Park Row

3:00-4:00pm Strolling Carolers

6:00pm Drawing of raffle of basket of goodies from local shops. Free ticket with every purchase.

6:00-7:00pm Mix and mingle with your community. Enjoy light bites and a store-wide discount for 15%, sponsored by Mercer Mountain Neighbors. All are welcome. The Chatham Bookstore, 27 Main Street.

Mulled Cider at The People’s Pub, 36 Main Street

Raffle and Pop-up shop for Handcrafted Herbals at The Warm Ewe, 31 Main Street

Clay handbuilding workshop All day with registration at iamround.com at Round Clay Studio, 25 Hudson Avenue

Fairy Hair Weaving and storewide sale at Red Mannequin in the Clocktower Building on Main Street

PopUp Shops Baker’s Addiction: baked goods, Chatham Animal Haven: crafted carpentry gifts, Carissa Fair: up-cycled wool sweaters, mittens, beaded Ukrainian Christmas spiders, stockings and ornaments, Kelly: jewelry and cards, SHOP 3 for 20% off sale. Roots Wholistic Wellness, 25 Main St.