Summer is winding down, but street festival season in Chicago is still going strong—here’s another event you won’t want to miss.
The 30th annual Retro on Roscoe festival is back in Roscoe Village this weekend (September 5-7), bringing three days of classic cars, live entertainment, and family-fun to Chicago’s north side.
What’s in store

The 2025 edition of Retro on Roscoe will feature more than 46 vintage cars and an appearance from the Oscar Mayer Weiner Mobile, making for some unforgettable photo ops.
Guests will also enjoy delicious local eats, live music across three stages, arts & craft vendors, kid-friendly activities, and more.
Retro on Roscoe is free to the public, with a $15 suggested donation. Proceeds will go towards supporting the Roscoe Village Neighbors association, a non-profit advocacy organization supporting the interests of the local community.
For more info about Retro on Roscoe 2025, click here.