Retro on Roscoe 2025: Chicago’s Time Machine Street Fest Turns Back the Clock

Chicago knows how to party like it’s 1985—or 1975, or even ’65. And this September, Roscoe Village once again transforms into a living, breathing time machine with the 30th Annual Retro on Roscoe Festival.

From Friday, September 5 through Sunday, September 7, the neighborhood becomes ground zero for nostalgia junkies and festival die-hards. Three stages blast out decades-spanning hits—everything from disco grooves to hair metal anthems—while side streets fill with chrome-dripping classic cars, vinyl-worthy vintage shopping, and a full-on retro carnival for the senses.

Foodies will find old-school bites and craft sips, kids can dive into family-friendly games and activities, and if you’re lucky, you’ll catch the legendary Weinermobile rolling through on Sunday from noon to 5 p.m. It’s not just a street fest—it’s a throwback block party that rewinds the soul of Chicago.

📍 Where: 2000 W. Roscoe St. (Damen to Leavitt, Roscoe Village)

🗓️ When: Fri, Sept. 5 (5–10 p.m.); Sat, Sept. 6 (Noon–10 p.m.); Sun, Sept. 7 (Noon–8 p.m.)

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