Retro on Roscoe

Friday 5pm – 10pm | Saturday & Sunday 12pm – 10pm

August 12-14, 2016

2000 W Roscoe St | Chicago

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 20th 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 $10 suggested donation. The Roscoe Village Neighbors are a non-profit organization comprised of volunteers that work hard daily to ensure committed excellence in advocacy of quality-of-life for Roscoe Village, its residents, and merchants alike.

To find out more about this event: Click Here

The Schedule

The Boy Band Night


East Stage
8:00PM Too White Crew
6:00PM Frisky Taylor


East Stage
8:00PM 16 Candles
6:00PM The Boy Band Night
4:00PM Cowboy Jukebox
2:00PM Blue Aura
12:00PM Robbie Gold

Center Stage
8:00PM Wedding Banned
6:00PM Mr. Blotto
4:00PM Little Queens
2:00PM MER
12:00PM LiveWire

West Stage
8:00PM Rod Tuffcurls & The Bench Press
6:00PM The Hat Guys
4:00PM South of 80
2:00PM Northside
12:00PM Sarah Marie Young

Kids Stage
1:00PM DJ
12:00PM Mary Macaroni


East Stage
8:00PM 7th Heaven
6:00PM Trippin Billies
4:00PM Planeta Azul
2:00PM Run Forrest Run
1:00PM Live Art by Cooney ArtWerks
12:00PM Extensions Dance Company

Center Stage
8:00PM American English
6:00PM Windbreakers
4:00PM Kashmir
2:00PM Stereo Heart
12:00PM Nicholas Barron

West Stage
8:00PM Who’s Bad
6:00PM One of These Nights
4:00PM Fletcher Rockwell
2:00PM Coyote Riot
12:00PM Aryk Crowder

Kids Stage
1:00PM DJ
12:00PM Mary Macaroni

retro final poster

The Live Music

3 days of live bands & musicians

Event Sponsors

Contact us for sponsorship opportunities

To sponsor Retro on Roscoe 2016, head over to our Sponsorships page

For Detailed Demographic Information: Click Here


Getting to 2000 W Roscoe


2000 W. Roscoe St.

From CTA Trains

Retro on Roscoe is located in Roscoe Village. If you’re planning on taking the train the Brown line is your best option. The Paulina stop is about 4 blocks east of the event.

From CTA Buses

If you’re planning on taking the bus, bus #50, which runs along Damen, will drop you off near the event at its Roscoe street stop.


Please Note: Vendors come August 13 & 14

(Only select food vendors and sponsors will be onsite Friday, August 12)

To sponsor Retro on Roscoe 2016, head over to our Sponsorships page

Be a Vendor


An artisan is a skilled manual worker who hand crafts items that may be functional or strictly decorative, including furniture, clothing, jewelry, household items, and tools.

Be a Vendor


Restaurants, grocery stores and institutional food providers selling food and non-alcoholic beverages.

Be a Vendor


A merchant is an entity who trades in commodities that he didn’t produce himself, in order to earn profit.

Be a Vendor

Non Profit

Charitable organizations that re building awareness. Please provide proof of non profit certificate with your materials.

IMPORTANT INFO: If you are applying as an ARTISAN or MERCHANT vendor, please submit at least 2 pictures of your artwork and/ or goods. Applications without will be rejected.