Retro on Roscoe

Retro on Roscoe returns Sept. 18-20 for its 31st annual edition: three stages, a six-block Roscoe Village footprint, family area, vintage shopping, 50+ classic cars/motorcycles, and a $15 suggested donation.

  • Dates: September 18–20, 2026
  • Where: 2000 W. Roscoe St
  • Neighborhood: Roscoe Village
  • Cost: Free

Schedule

  1. Sept. 18 — Friday: 5-10 p.m.
  2. Sept. 19 — Saturday: Noon-10 p.m.; family programming, car/motorcycle show energy, three stages, and vendor browsing.
  3. Sept. 20 — Sunday: Noon-8 p.m.; calmer family and neighborhood day.

What to expect

Roscoe Village's vintage-and-throwback street fest, September 18–20, 2026 on Roscoe Ave between Damen and Leavitt. The pitch is a deliberately retro vibe: classic car show (1950s–80s), live music spanning oldies, soul, motown, '80s tribute bands, vintage clothing and decor vendors, and the neighborhood's bars/restaurants spilling onto the street. End-of-summer feel — September weather, smaller crowds than peak fests, friendlier.

Tickets

Free to enter in the street-fest sense; Roscoe Village Neighbors lists admission as a $15 suggested donation. The donation supports Roscoe Village Neighbors, a 501(c)(3). Optional VIP and wine/spirits tasting tickets are listed as coming soon by Special Events Management and are separate from general entry.

Transit

Brown Line to Paulina is a 5-minute walk; the 50 Damen and 77 Belmont buses both stop within a block. Driving is rough; permit-only side streets. Try Ashland or Western and walk in.

Bag policy

No formal bag check; ID at beer tents.

Family-friendly

Family-friendly, especially for kids who love cars — the classic car show is a real draw and lets kids look (don't touch) at vintage Mustangs, Camaros, T-Birds. Stroller-easy on Roscoe Ave. Cooler September weather is more comfortable for kids than peak summer fests. Restrooms via porta-johns and participating bars.

Local tips

  1. Saturday is for the car show and family area; Sunday is for lower-stress browsing.
  2. Do not call the $15 a ticket. Roscoe Village Neighbors uses suggested-donation language, which matters for trust.
  3. The 2026 band lineup is not posted yet. SEM currently shows last year's performers as reference, not this year's schedule.
  4. The VIP/tasting options are comfort add-ons, not required admission. Watch for final on-sale if shade/bathrooms matter to your group.
  5. Pair the festival with a slow walk on Roscoe's residential side streets; the neighborhood setting is the charm.

Frequently asked questions

When is Retro on Roscoe 2026?

Friday, September 18 from 5-10 p.m.; Saturday, September 19 from noon-10 p.m.; and Sunday, September 20 from noon-8 p.m.

Is admission free or ticketed?

General street-fest entry is not a hard ticket. Roscoe Village Neighbors lists a $15 suggested donation.

What supports the donation?

The beneficiary is Roscoe Village Neighbors, a 501(c)(3) nonprofit that supports neighborhood quality of life, business vitality, community programs, and local advocacy.

Is the 2026 music lineup posted?

Not yet. Special Events Management says bands are still being booked and currently shows last year's performers as reference.

What is the family highlight?

The family area includes inflatables, crafts, balloon artists, face painting, music, rides, and the antique/classic car and motorcycle show.

Official festival information