Time-Travel Is Coming to Roscoe Street: Retro on Roscoe Gets a Major Sponsor — and the Village's Fall Calendar Is Stacked

By Socialhood News · Il/Chicago/Roscoe Village · July 31, 2026

Summer isn't even over, but Roscoe Village is already making big moves for fall. Retro on Roscoe — one of Chicago's most beloved street festivals — has officially landed a presenting sponsor: Wells Fargo. The newly branded "Retro on Roscoe, presented by Wells Fargo" is set for September 18–20, 2026, promising the neighborhood's signature blast-from-the-past vibes with an even bigger platform behind it. Hosted by Roscoe Village Neighbors, the three-day festival transforms Roscoe Street into a retro wonderland of vintage culture, classic cars, music, and community fun. Vendors interested in joining the festivities can register directly through roscoevillage.org.

Before you dust off your vintage threads, though, there's plenty happening in the weeks ahead. The Lakeview Taco Fest is just three weeks away, running August 21–23 along the Lakeview corridor. And if you're looking ahead even further, the brand-new Lincoln Brunch Fest hits the calendar on October 10, followed by the Lincoln Roscoe Beer Stroll on October 17 — giving the neighborhood a packed run of events straight through autumn.

Want to help shape what's next for the Village? Roscoe Village Neighbors holds its next community meeting on Wednesday, August 19 at 6:30 p.m. — a great opportunity to plug in, meet your neighbors, and have your voice heard. Stay up to date at roscoevillage.org and lakeviewroscoevillage.org.

Sources:
1. https://www.roscoevillage.org/
2. https://www.lakeviewroscoevillage.org/