Chatham Winterfest

Village of Chatham Winterfest 2025

Saturday, December 13 • 11:00 AM – 4:00 PM
Chatham, NY

Chatham, NY, November 29, 2025 — The Village of Chatham, NY will host its beloved annual Winterfest on Saturday, December 13, 2025, transforming Main Street into a lively holiday celebration from 11:00 AM to 4:00 PM. Residents and visitors are invited to enjoy a festive lineup that includes a cookie contest, live music, jugglers, strolling carolers, hay wagon rides, family activities, and more throughout the village.

Event Highlights

11:00 AM – 1:00 PM:

• Visit with Santa Claus at the Crandell Theater until noon. Afterward, Santa will stroll along Main Street until 1:00 PM.

11:30 AM:

• Cookie Contest — Deliver entries by 11:30 AM at the Crandell Theater. Judging begins at 12:00 PM in the Crandell lobby. Cash prizes awarded.

Noon:

• Book Signing at The Chatham Bookstore, 27 Main Street
  Conrad Vispo will sign copies of From the Hudson to the Taconics: An Ecological and Cultural Field Guide to the Habitats of Columbia County.

Noon – 1:00 PM:

• Ragamuffins Juggling Act performing along Main Street.

Noon – 4:00 PM:

• Wine & Cheese Tasting at Chatham Wine & Liquor, 53 Main Street
• Live Music & Tasting with Ten Mile Distillery at Park Row Gallery, 57 Main Street

1:00 – 2:40 PM:

• Free Screening of The Polar Express at the Crandell Theater

2:30 – 4:00 PM:

• Strolling Carolers throughout the Village

All-Day Activities

• Hayrides & Candy Canes (weather permitting) departing from the intersection of Park Row and Main Street
• Christmas School Bus with kids’ activities in the Hudson Valley Credit Union parking lot next to the Crandell Theater
• Gift Wrapping at Tracy Memorial Hall, 77 Main Street
  Donations benefit the Ghent and Chatham food pantries. Supplies provided by Connect Ghent and Chatham For All.
• Holiday Ornament Sale featuring local artisans at Round Clay Studios, 25 Hudson Avenue
• Soap & Scented Candle Sale at Concord Hill Soap and Candle, 54 Main Street
• Eggnog at Boxwood Linen, 22 Main Street
• Village-Wide Holiday Raffle — Receive a free raffle ticket from every store you visit for a chance to win a basket of gifts from Chatham merchants.
• Seasonal Fare at Local Restaurants, including spiced hot chocolate and hot mulled cider at Bimi’s Cheese Shop

Celebrate the Season in Chatham

Chatham’s Winterfest is a cherished community tradition, offering something for all ages and bringing neighbors and visitors together to kick off the holiday season. Come enjoy a full day of festive cheer, local shopping, family fun, and small-town holiday spirit.