Retro on Roscoe
2026-09-18 17:00 - 2026-09-20 20:00 UTC | Roscoe Village, Roscoe St. & Damen Ave., Chicago, IL, 60657, United States
Ever wish you could go back in time? Well here’s your chance! Referred to by Patch as a “Generation X haven”, Chicagoans looking for a blast from the past don’t need to look further than the 31st annual Retro on Roscoe festival. Go back in time with music enthusiasts, families, and gearheads for a back in the day weekend.
Three stages will be spread amongst an eminent six-block stretch in Chicago’s favorite Roscoe Village. Live music will play oldies and throwbacks along with popular hits to keep festival goers moving through the hot summer nights! The soundtrack for the annual Retro on Roscoe will be the bomb!
The beautiful tree-lined streets of Roscoe Village will set the scene for artisans, antique vendors and cool merchants in an offbeat shopping atmosphere that is second to none. Roscoe Village’s top restaurants will also serve up much-desired summer treats that will keep the whole family pleased.
After eating some small bites make sure to head over to the family area that offers prime inflatables, delectable crafts, balloon artists, face painting, music, rides and more. Once the kids have their dose of entertainment, put the pedal to the metal with 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.
Admission to Retro on Roscoe is a $15 suggested donation.

Roscoe Village Halloween Block Party
2026-10-18 12:00 - 17:00 | Roscoe Village, Roscoe St. & Damen Ave., Chicago, IL, 60657, United States
Save the date for the Roscoe Village Halloween Block Party! Celebrate the season in a safe, outdoor, family-oriented environment on Roscoe. Wear your costume and join us for Halloween themed activities and more! Look for more details to be released soon.
When: October 18, 2026
Where: On Roscoe Street between Damen and Hoyne.

Roscoe Village Winterfest
2026-12-05 17:30 - 2026-12-06 16:00
