Retro on Roscoe 2026

Details Friday, September 18, 2026 | 5:00pm to 10:00pm Saturday, September 19, 2026 | 12:00pm to 10:00pm Sunday, September 20, 2026 | 12:00pm to 8:00pm Retro on Roscoe (Sept 18-20, 2026) – 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 18-20 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!