Retro on Roscoe Festival

Go back in time and enjoy oldies and throwback fashion at the 28th annual Retro on Roscoe festival on September 5-7, 2025, in the Roscoe Village neighborhood.

Photo courtesy of Retro on Roscoe

Groove to music on three stages, including a family stage, within a six-block stretch of Roscoe Village. Enjoy music from the 70s, 80s and 90s with featured bands including 16 Candles, Too Hype Crew and Mr. Blotto.

Browse artisans, antique vendors and merchant shops. Roscoe Village’s top restaurants will also serve up street food and treats. Head over to the family area that offers inflatables, crafts, balloon artists, face painting, music and carnival rides.

Photo courtesy of Roscoe Village

Check out the Antique and Classic Car and Motorcycle Show. Presented by Four Treys Bar, Retro’s Antique Car Show will showcase over 50 antique, classic and muscle cars throughout the festival weekend.

This year’s fest will feature special wine and spirits tastings on Saturday and Sunday afternoons. Tickets will be on sale for two hour sessions with eight different wines and spirits to sample.

Retro on Roscoe runs from 5-10 pm on September 5 and from noon to 10 pm on September 6 and 7, at 2000 W. Roscoe St. The event is free with a $10 suggested donation.