Roscoe Village's Annual Winterfest Returns December 6-8 with Tree Lighting, Holiday Market, and Family Activities

By Socialhood News · Il/Chicago/Roscoe Village · November 30, 2025

Roscoe Village residents can mark their calendars for the neighborhood's beloved annual Winterfest celebration, scheduled for December 6-8, 2025. The festive weekend will kick off Friday evening with a Holiday Happy Hour at Le Sud from 5-7 PM, followed by Saturday's highlight event—the Roscoe Village Tree Lighting Ceremony at 5 PM at 2200 W. Roscoe Street.

The three-day celebration promises a full schedule of seasonal activities including shopping at one-of-a-kind boutiques, hot chocolate stations, holiday cider, caroling, and a special Holiday Market featuring local businesses with exclusive promotions. Sunday's family-friendly lineup includes visits with Santa Claus at Cubbington's Cabinet from 1-5 PM and horse-drawn sleigh rides through the neighborhood. The event showcases Roscoe Village's distinctive small-town charm while supporting the area's vibrant independent business community.

Residents and visitors are encouraged to register for the opening Happy Hour on the Roscoe Village Neighbors website and to explore the participating businesses' special offerings throughout the weekend. This annual tradition offers the perfect opportunity to connect with neighbors while experiencing the warmth and community spirit that makes Roscoe Village one of Chicago's most cherished neighborhoods during the holiday season.

Sources:
1. https://www.roscoevillage.org/winterfest/