Free Meet Me on Milwaukee

Roaming through car-free streets is one of the joys of Chicago street fests and just because the summer is over doesn’t mean you can’t still experience this favorite pastime.  Head to the Wicker Park neighborhood for the Meet Me on Milwaukee event, where the busy intersection of Milwaukee at the North and Damen intersection will be closed to traffic on October 26, 2026.

Photo courtesy of Meet Me on Milwaukee

Explore the iconic street and all the shops and restaurants that will set up sidewalk displays while dancing to live music, walking and discovering new treasures and sales.

The event kicks off on the last Sunday in August, September and October with special giveaways and pop-ups.  Meet Me on Milwaukee runs from 10:00 a.m. to 5:00 p.m. and admission is free. Check out these participating community businesses during the event:

Neighborly        

Oro Chocolate & Coffee        

HealthSource of Chicago Wicker Park        

NINADNGR, Silhouette Portraits, T2D2 Toys         

Wanna Vintage        

Volumes Bookcafe        

Flat Iron Arts Building        

Topdrawer        

The Exchange        

ONYX Reformer Pilates        

Transit Tees (North)        

store B vintage        

Jackson Junge Gallery        

Buffalo Exchange        

Mojo Spa        

BODEGA VINTAGE LLC        

Jackson Junge Gallery        

BODYBAR Pilates        

Transit Tees (South)        

Phil Circle Music        

Demolition Collective         

Canine Cruise        

Recklace Records        

The Den Theatre        

Black Luxe Candle Co.

Meet Me on Milwaukee

Milwaukee between Damen and North Ave.

October 26, 2025

Free

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