2023 Winter Walk on Wilson

2023 Winter Walk on Wilson

2023 Winter Walk on Wilson
Friday, December 1st
5:00pm – 8:00pm


The Uptown Chamber of Commerce is hosting our 9th Annual WINTER WALK ON WILSON on Friday, December 1, 2023 from 5:00 – 8:00 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!

Stroll along Wilson Avenue to experience the holiday cheer of live performances and free tasty offerings by Uptown's small businesses!  The first 20 people to stop by each of the participating businesses will receive an LED Snow Globe pin.  Wear this during the event 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!   Full list of participating businesses here

Step inside the Uptown Holiday Market hosted by the Chicago Market at 4620 N. Broadway featuring 30 retail vendors, kids crafts, and photo ops with Uptown's own Panda Claus!   Full list of vendors here

Winthrop Family Historical Garden, 4628 N. Winthrop

Have you heard?  Be vigilant! The snow whale is coming back after 100 years away in honor of the Uptown Chamber's 100th Anniversary! On the first of December! The snow whale!  It’s coming back!   
Don’t miss you chance to compose your message of holiday hope to share with the snow whale and seal your message in a decorated bottle, and cast it into the boat shrine floating upon the winter sea. 
A variety of performers and strolling musicians will be playing along the Wilson Avenue corridor including street corners and inside local businesses.  Confirmed performers include:  Faces for Radio, The People’s Music School, The Red Line Hustlers, Coffee Jazz Collective, Beaux & Belles, Aloha Center Chicago, Cabinet of Curiosity, The Crossing, Glenn Kaiser, Old Town School of Folk Music + more TBA. 
Special Drink Discounts (ages 21+):
Make your way to our participating bars to take advantage of special drink discounts and offers (ages 21+ only)!  Participating Bars include:  

  • 2Bears Tavern - $3 house shots, $7.50 Big Miller Lites.  Offer good during open hours - 3:00PM to 4:00AM
  • Carol’s Pub -  $7 old fashioneds and margaritas. Offer good from 5:00PM - 8:00PM
  • Max’s Place - $4 Chicago Handshakes (12oz Old Style Draft and a shot of Malort), $3 Draft beers. 5:00PM - 8:00PM
  • My Buddy’s -  $1 of EVERY Drink purchase AND $2 of any shot or Specialty Drink (Mojito, Margarita, Old Fashioned, etc) will go to support the Pedersen-McCormick Boys & Girls Club!  Offer good during open hours -5:00PM - 2:00AM
  • XMarket Food Hall - Free tea samples & Half off margaritas and mules.  5:00PM - 8:00PM


FREE PARKING available until 8:30pm in Truman College’s parking garage (directions) located off of Racine Street, and is accessible from Wilson Avenue.


Thank you to our 2023 Winter Walk on Wilson sponsors!


Presenting Sponsors:




Map Sponsor:


Event Sponsor:



Thank you to our 2023 Annual Sponsors!















DLG Management
Platform 4611
Tiny Giants



Longford Construction



Date/Time December 1 2023, 5:00pm - 8:00pm
Location Wilson & Broadway 
A map of participating business will be announced soon!