Retro on Roscoe

Details

Friday, September 18, 2026 | 5:00pm to 10:00pm
Saturday, September 19, 2026 | 12:00pm to 10:00pm
Sunday, September 20, 2026 | 12:00pm to 8:00pm
logo retrocircle 300x300

Overview

Retro on Roscoe (Sept 18-20, 2026) – A Blast from the Past in the Heart of Chicago! 🎸🚗🎡

Get ready to time-travel at Retro on Roscoe, one of Chicago’s most beloved street festivals, happening September 18-20 in the charming Roscoe Village! This throwback extravaganza is packed with live music, classic car shows, vintage shopping, and old-school fun for all ages.

Stroll down Roscoe Street and soak in the nostalgic vibes, from decades-spanning hits on multiple stages to rows of rare and restored classic cars gleaming in the sun. Indulge in delicious eats from top local vendors, sip on craft beer, and let the kids enjoy the family-friendly games and activities in the dedicated children’s area.

Whether you’re a rock ‘n’ roll fanatic, a vintage lover, or just here for the good times, Retro on Roscoe is your ticket to a fun-filled weekend of music, memories, and retro magic! ✌️🎶🚀

For more information on Retro on Roscoe including entertainment line up, vendors and sponsorship opportunities, see the tabs below.

We’re busy booking bands, bands and more bands. Check back soon with all the tea.

Here’s who performed last year:

Friday
5:30pm – Pino Farina Band
8:00pm – 16 Candles

Saturday
Noon – Aimont Moon
2:00pm – Boots in Transit
4:00pm – Whatever, Nevermind: Nirvana
6:00pm – KASHMIR
8:00pm – ROK Brigade

Sunday
Noon – Fallen Idol
1:45pm – Square Cut Band
3:45pm – Stache
6:00pm – Rod Tuffcurls & The Bench Press

More bands!  Who do you want this year?  Check back soon to see who we picked!

Here’s who we had in 2025:

Friday
5:30pm – South of 80
8:30pm – The Buckinghams

Saturday
Noon – UpBeat Music & Arts Program
2:00pm – Into The Heart: U2 Tribute
4:00pm – Run Forrest Run
6:00pm – Our Name is Jonas
8:30pm – Dancing Queen: An ABBA Salute

Sunday
Noon – Blind Reality
2:00pm – Santeria: Sublime Tribute
4:00pm – Too Fighters: Foo Fighters Tribute
6:00pm – Hello Weekend

3 stages of non-stop music is A LOT of music — but oh so fun!  Check back soon for who we’re bringing on this year.

In the meantime, here’s who performed last year:

Friday
5:00pm – Fiddlerock!
6:30pm – Full Volume Band
8:00pm – Rosie & The Rivets

Saturday
2:00pm – Amanda Coppotelli
4:00pm – 3 Martini Jeannie
6:00pm – Funky Monks: RHCP Tribute
8:00pm – Trippin Billies

Sunday
2:30 pm – Jagged Little Pill
4:30pm – Big Bang Baby: STP Tribute
6:30pm – The Gingers

We know you’re a VIP but make sure everyone else knows the same!

COMING SOON!

$45
Choose from one of these days … 
Friday – 5pm-10pm
Saturday – 5pm to 10pm
Sunday – 5pm to 8pm
What you get:
– 2 drink tickets
– private bar with specialty drinks
– private shaded seating area
– private bathrooms
– complimentary food bites from local restaurants
** Opportunity to purchase a tasting ticket for only $22.

Whether you’re starting or ending your day with a tasting, it’s a great chance to sip something you’ve never tried before!  Join us for the 2nd annual Wine & Spirits Tasting on Saturday & Sunday afternoon!

COMING SOON!

$30
Sessions … 
Saturday – 12pm to 2pm AND 2:30pm to 4:30pm
Sunday – 12pm to 2pm AND 2:30pm to 4:30pm
What you get:
– sample up to 8 different types of wine or spirits
– private shaded area to enjoy your samples
– private bathrooms

Roscoe Village Neighbors, a 501(c)(3) nonprofit organization, serves the Chicago community bounded by Addison Street and Belmont Avenue from Ravenswood Avenue on the east to the Chicago River on the west.

Serving as a committed advocate for the community of Roscoe Village, Roscoe Village Neighbors (RVN) seeks to enhance the quality of life of both its residents and merchants by:

  • serving as a liaison to information and resources
  • giving back to the community with philanthropic initiatives
  • offering social activities that bring the community closer
  • providing a forum for its members to discuss issues impacting the community
  • organizing timely responses to issues to help ensure that community opinions are heard

Our primary purposes, as set forth in our bylaws, are to:

1. Work with public officials, private citizens, and block clubs to ensure the quality and availability of public and private community services and maintain the safety and mobility of the people who live and work in Roscoe Village;

2. Promote Roscoe Village as a place to conduct business and facilitate the development of a vital and prosperous business community;

3. Collect and distribute information about topics of interest to the community and provide a forum for residents, block clubs, and business owners to express their opinions;

4. Gain consensus on such topics and speak as a uniform voice for the community; and,

5. Promote a spirit of cooperation, goodwill and neighborliness, and encourage people to openly communicate and participate in the exchange of ideas about how to improve the community and preserve those features that make this community unique.

Looking to connect with active consumers at this event? For pricing and a customized benefits package, please contact Karyn Terrones at karyn@chicagoevents.com or 773-584-6625.

Coming soon!