Festivals, Fairs & Special Events
Retro on Roscoe 2026 September 20, 2026
Get ready to time-travel at Retro on Roscoe, presented by Wells Fargo, one of Chicago’s most beloved street festivals, happening September 18–20 in 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 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, presented by Wells Fargo, is your ticket to a fun-filled weekend of music, memories and retro magic.
Learn more about the area
Neighborhood
Roscoe Village
A village within a city, you’ll feel right at home amid cozy cafes and cute shops.
Learn more about the area
Neighborhood
Roscoe Village
A village within a city, you’ll feel right at home amid cozy cafes and cute shops.
