Event Details
CHICAGO, September 2026— Ever wish you could go back in time? Chicagoans looking for a blast from the past don’t need to look further than the 31st Annual Retro on Roscoe festival. Get ready to time-travel at Retro on Roscoe, one of Chicago’s most beloved street festivals, happening Friday-Sunday September 18-20 in the charming Roscoe Village! This throwback extravaganza is packed with live music, a classic car show, vintage shopping, and old-school fun for all ages. Located at 2000 W Roscoe St. from Damen to Leavitt, the fest will be held Fri-Sun, Sept. 18-20. Visit Fri 5-10 p.m.; Sat- Noon - 10 p.m. and Sun. Noon – 8 pm.
Stroll down Roscoe Street and soak in the nostalgic vibes, from decades-spanning hits on two stages. Each day, check out the classic car show. Indulge in delicious eats, see top arts & crafts vendors, sip on wine and spirits, and let the kids enjoy the family-friendly games and activities in the dedicated children’s area.
Live music will play oldies and throwbacks along with popular hits to keep festival goers moving.
Music acts include:
West Stage Entertainment
Friday
5:30pm – Stache
8:00pm – Dancing Queen: An ABBA Salute
Saturday
12:30pm – Aimont Moon
2:00pm – Blind Reality
4:00pm – Lil’ Ed & The Blues Imperials
6:00pm – Rearview (Pearl Jam Tribute)
8:00pm – Abbey Road: The All-Star Beatles Rockestra
Sunday
12:00pm – Golden Fiddle
1:30pm – 88 Keys
3:00pm – The Divas
5:00pm – Sixteen Candles
7:00pm – Dance worthy music to finish the night!
East Stage Entertainment
Friday
5:30pm – South of 80
8:00pm – Boy Band Review
Saturday
12:00pm – Boots in Transit
2:00pm – Sam Fazio Quartet
4:00pm – The PriSSillas
6:00pm – Fearless: A Tribute to Taylor
8:00pm – Hello Weekend
Sunday
12:00pm – School of Rock
1:30pm – RAVIV
3:00pm – Super Creeps
5:00pm – Trippin Billies
“We are thrilled to celebrate the 31st annual Retro on Roscoe,” said Brian Crouch, President of the Roscoe Neighbors Organization “Thanks to all fest attendees, the suggested gate donation helps keep this annual fest strong for all to enjoy. The donations benefit the invaluable programs and services of the Roscoe Village Neighbors, a 501(c)(3) nonprofit organization, serves the Chicago community bounded by Addison Street and Belmont Avenue from Ravenswood Avenue on the east to the Chicago River on the west.
As a non-profit organization and not city funded, donations will help these festivals stay around for all to enjoy.
A $15 donation is suggested. For more information, visit chicagoevents.com/event/retro-on-roscoe/
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