The holiday season is coming to Roscoe Village. Roscoe Village Winterfest returns Saturday, December 5, and Sunday, December 6, 2026, with a weekend of neighborhood celebrations and holiday cheer.
Organized by Roscoe Village Neighbors, Winterfest celebrates the neighborhood’s local businesses and community traditions with family-friendly activities, seasonal treats and opportunities to shop locally.
A weekend to celebrate Roscoe Village
Expect a festive neighborhood atmosphere, holiday shopping and activities for families. Winterfest is also a timely reminder of how much the independent stores and restaurants along Roscoe Street contribute to the neighborhood’s character.
Earlier Winterfest celebrations have featured visits with Santa, special shopping events and other seasonal attractions. The full activity-by-activity 2026 schedule has not yet been confirmed in the listings reviewed, so those past features should not be treated as guaranteed for this year.
Roscoe Village Winterfest 2026: Event details
- Dates: Saturday, December 5–Sunday, December 6, 2026
- Location: Roscoe Village, Chicago
- Organizer: Roscoe Village Neighbors
- Published event window: Saturday from 5:30 p.m. through Sunday at 4 p.m.; individual activity times may differ
For the latest programming, exact locations and any schedule changes, check the Roscoe Village Neighbors Winterfest event page and the Chamber’s event calendar.