Winter Walk on Wilson

Winter Walk on Wilson
Friday, December 5th
5:00pm – 8:30pm
FREE EVENT! RSVP to win prizes!

The Uptown Chamber of Commerce is hosting our 11th Annual WINTER WALK ON WILSON on Friday, December 5th, 2025 from 5:00 – 8:30 PM. This FREE event features sweet treats, warm drinks, and menu samples offered by local Uptown businesses and organizations, live holiday music along the Wilson and Broadway commercial corridors, a pop-up holiday market, and photo ops with Uptown’s own Panda Claus!

PRIZE ALERT #1: The Uptown Chamber will be awarding prizes to a select few who RSVP for this free event! Click here.

5:00-8:30PM
Small Business Activations!
Stroll along Wilson Avenue to experience the holiday cheer of live performances and tasty offerings by Uptown's small businesses!

PRIZE ALERT #2: Help us light the night by wearing anything that lights up for your chance to be spotted and awarded a surprise gift from the Uptown Chamber of Commerce including gift cards to local businesses and swag!

Participating Uptown small businesses/orgs:
Stay tuned for a list of participating businesses and a digital map!

5:00 - 8:30PM
Music and Caroling!
Performers and locations TBA

5:00-8:30PM
Uptown Holiday Market!
Chicago Market, 4618 N. Broadway
Step inside the Uptown Holiday Market featuring retail vendors, kids crafts, and photo ops with Uptown's own Panda Claus! Gift wrapping provided by Friends of McCutcheon Elementary (donations accepted). Click here for vendor application.