Retro on Roscoe

Retro on Roscoe (Sept 5-7, 2025) – A Blast from the Past in the Heart of Chicago! 🎸🚗🎡

Get ready to time-travel at Retro on Roscoe, one of Chicago’s most beloved street festivals, happening September 5-7 in the charming Roscoe Village! This throwback extravaganza is packed with live music, classic car shows, vintage shopping, and old-school fun for all ages.

Stroll down Roscoe Street and soak in the nostalgic vibes, from decades-spanning hits on multiple stages to rows of rare and restored classic cars gleaming in the sun. Indulge in delicious eats from top local vendors, sip on craft beer, and let the kids enjoy the family-friendly games and activities in the dedicated children’s area.

Whether you’re a rock ‘n’ roll fanatic, a vintage lover, or just here for the good times, Retro on Roscoe is your ticket to a fun-filled weekend of music, memories, and retro magic! ✌️🎶🚀

You may also like the following events from Special Events Management:

• Next Friday, 22nd August, 04:00 pm, Lakeview Taco Fest in Chicago
• This October, 3rd October, 05:00 pm, Lincoln Park Wine Fest in Chicago

Also check out other Kids events & activities in Chicago, Music events in Chicago, Festivals in Chicago.