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!

Click here for digital map and guide!

FREE PARKING is available until 9:00pm in Truman College’s parking garage (directions) located off of Racine Street, and is accessible from Wilson Avenue.

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

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!

5:00-8:30PM
Small Business Activations!
Stroll along Wilson Avenue to experience the holiday cheer of live performances and varied offerings by Uptown's small businesses including holiday treats, menu samples, free classes, crafts for both kids & adults, and more!

Participating Uptown small businesses/orgs: Click here for digital map and guide!

5:00 - 8:30PM
Music and Caroling!
Catch these roaming performers along Wilson Avenue on the night of the event:

Beaux & Belles
Cabinet of Curiosity
Faces for Radio
Grrr Records (Hilde Bialach & Glenn Kaiser)
Lakeside Pride Instrumental Carolers
The People's Music School
The Pippins

5:00-8:30PM
Uptown Holiday Market!
Chicago Market, 4618 N. Broadway
Note: this space is ADA accessible and pet-friendly!

Step inside the Uptown Holiday Market featuring 40+ vendors and photo ops with Uptown's own Panda Claus! CLICK HERE for vendor listing + items to be featured.

SHOP LOCAL this holiday season! Starting on Friday, December 5th at the Winter Walk on Wilson, you can take home an Uptown branded, insulated 11oz tumbler with any purchase of $50 or more at these retail locations. Giveaway will continue while supplies last!

Aquarius - 1344 W Wilson Ave
Broadway Bikes - 4653 N Broadway
Chicago Fair Trade Museum - 4704 N Broadway
Foursided - 5061 N Clark St
Haitian American Museum of Chicago - 4654 N Racine Ave
Miniso - 5004 N Broadway
Poor Boy Rich Taste -  1216 W Wilson Ave
Qideas Plants & Gifts - 1134 W. Argyle St
TERRACE -  1329 W Wilson Ave
Trading Post Pet Supplies -  4747 N Clark St
Urban Pooch Canine Life Center -  4501 N Ravenswood Ave

BONUS: Show your receipt of any purchase from the Uptown Merch Shop and pick up a free tumbler on Friday, December 5th from 5:00-8:30pm at the Uptown Info Booth at our Holiday Market (4620 N. Broadway). Limit one per customer.

Thank you to our 2025 Presenting Sponsors!