7th Annual Winter Walk on Wilson
Friday, December 3rd, 2021
5:00pm – 8:00pm

The Uptown Chamber of Commerce is hosting our 7th Annual WINTER WALK ON WILSON on Friday, December 3, 2021 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, Broadway, and Clark commercial corridors, pop-up holiday markets, and photo ops with Uptown’s own Panda Claus!

To comply with current COVID guidelines, all attendees will be required to wear a mask when entering any of our participating Uptown businesses.

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

Strolling performances
by The People’s Music School, Lakeside Pride Music Ensembles, Old Town School of Folk Music, and more!



6:30-7:30pm – Check out the 12 ft. tall Caroling Goddess (Cabinet of Curiosity) right outside the Wilson CTA station!


5:00-8:00pm – Stop by these participating businesses for some treats and live music! See map image for addresses:

Hearthstone & Terrace
– 1329 W. Wilson
Ghirardelli hot chocolate from Crema Shop, delicious treats from Misericordia, Heart of Mercy’s Hearts & Flowers bakery , spiced (& spiked ) winter cider, samplings of JuneShine hard kombucha

Kāl’ish 1313 W. Wilson
Biscoff s’more soft serve

Sam & Gertie’s 1309 W. Wilson
Chanukah Latke Tots

Pokiology 4600 N. Magnolia (entrance on Wilson)
Poke & Tofu samples

Wagnolia Vet 4600 N. Magnolia
Hot chocolate, cider, and peppermint candies PLUS dog and cat treats and holiday safety tips handouts for pets!

Spoil Me Hair Salon & Spa 4668 N. Broadway
Hot Cocoa Bar with ALL the fixings

upshore chapter apartments: 4555 N. Sheridan
Assorted treats in the lobby plus tours of the building leaving from the lobby at 5:30, 6:00, 6:30, 7:00pm

Everybody’s Coffee 935 W. Wilson
Hot decaf mint tea, hot drip coffee (Feliz holiday blend), mini chocolate chip cookies, and GF vegan peppermint mocha brownie bites

Wilson Abbey Windows 935 W. Wilson
Window #1 revealed for the Biggest Advent Calendar in Chicago (look up!!!)


5-8pm: Chicago Market – Holiday Pop-Up Market (4620 N. Broadway) featuring:
*Several amazing local vendors
*Selfie opportunity with Uptown’s very own Panda Claus!!
*Art Making Corner (all ages): Creating Art with Sharon Hyson, ATR, Art Therapist Educator
5:00 Box Puppet Making
6:00 Winter Mobiles and Unity Sticks
7:00 Make a Mini Grateful Book


5-8pm: Uptown Business Center Pop-up (1124 W. Wilson) featuring:
*Discover Virtual Reality with Redline VR!
*Meet DiDa Ritz from Season 4 of RuPaul’s Drag Race at the Dispensary 33 booth!
*Get updates on the CTA RPM Project which modernizes our public transportation system to strengthen communities, serves riders and stimulates inclusive economic growth
*CircEsteem will be on hand to demonstrate mat skills as part of their circus arts programming!
*Artwork by Abena Motaboli


8:00pm – AFTER-PARTY at Carol’s Pub (4659 N Clark St) including free cover when mentioning Winter Walk on Wilson (offer good from 7:30 – 9:00pm) to see Scott Dubose and the 101 Ranch
All participants get:
*Hot Cocoa – participants can add a liquor shot of choice if staying at Carol’s. If leaving, participants can take Cocoa out – 4p-8p
*Participants will also receive a wooden coin token to use at a later date or later that night that is good for a free draft beer or well drink.
*Want to make it a Pre-party? Check out their Happy Hour Specials from 4p-7p!

Participating businesses: 

Carol’s Pub
Chicago Market – Holiday Market: featuring 20+ vendors
Uptown Business Center (featuring pop-ups by Redline VR, Dispensary 33, CTA, CircEsteem, + Artist – Abena Motaboli)

Everybody’s Coffee
Hearthstone & Terrace
Sam & Gertie’s
Spoil Me Hair Salon & Spa
Upshore Chapter Apartments
Wagnolia Veterinary Clinic
Wilson Abbey


Thank you to our 2021 Annual Sponsors!