Overview Retro on Roscoe is a three-day throwback street festival in Chicago's Roscoe Village, closing Roscoe Street at Damen Avenue for two stages of tribute bands, a vintage and antique market and more than 50 antique, classic and muscle cars parked along the blocks. It runs Friday evening through Sunday in September. Roscoe Village Neighbors, the neighborhood's 501(c)(3) association covering Addison to Belmont and Ravenswood to the Chicago River, puts it on as its main fundraiser, and Special Events Management produces it. On site The music runs on a West Stage and an East Stage, and most of the bill is tributes. The 2026 lineup had Dancing Queen: An ABBA Salute and Boy Band Review on the Friday night, then Abbey Road: The All-Star Beatles Rockestra, a Pearl Jam tribute called Rearview and Fearless: A Tribute to Taylor on the Saturday, with Lil' Ed and the Blues Imperials playing blues in the afternoon and School of Rock opening Sunday on the East Stage. Artisans, antique dealers and neighborhood merchants set up along the street, local restaurants serve food and drink, and the car show stays parked all weekend. A family area carries inflatables, crafts, balloon artists, face painting and rides. In 2025 the festival added a VIP and tasting experience, 21 and over, with wine and spirits tastings and a lounge. Audience The festival is run by the people who live around it: Roscoe Village Neighbors counts more than 400 volunteers working it each year. The program splits between families, who have the kids area, and adults, who have the beer, the tasting lounge and the cover bands playing into the night. Track record The 2025 edition was the festival's 30th. The money it raises pays for the neighborhood's streetscape projects, park improvements and school resources, and for Roscoe Village Neighbors' other events, including its Halloween celebration and Winterfest. Brand presence Wells Fargo presented the 2026 festival, with State Farm and CVS Health among the other sponsors. Partners come in at three levels, top, mid and entry, and the car show carries its own presenting name; in 2025 that was Four Treys Bar.