A spiritual successor to the Cutting Crew Classic, we're bringing back the yearly mega race that the community used to cherish, as well as events like Messenger Prom, and Messenger Olympics, celebrating what it means to be a lover of cycling, free spirited and gnarly. So Join us and register before May 22nd below! Non-Bike Messengers also encouraged!

REGISTER HERE

Cash App

REGISTRATION

Full Weekend Pass + T-Shirt
$55
Just T-Shirt
$20
Just Friday Pre event
$15
Just Saturday Main Race + Prom
$35

Choose your pricing plan

Find one that works for you

Best Value
Full Weekend Pass + T-Shirt!
55$
Access to the entire Weekend's Races, Parties, Messenger Prom, Messenger Olympics, and your official Limited Edition Chicago Courier classic T Shirt!
Valid for one month
- Access to Friday and Saturday's Races
- Guaranteed ticket to all parties including Messenger Prom!
- Limited Edition 100% Cotton Gilden T Shirt!
Just Main Race + Prom
35$
Registration for the Chicago Courier Classic Race on Saturday + access to the Messenger Prom following the race!
Valid for one month
- Registration for Main Race
- Guaranteed ticket to Messenger Prom!
Just Going Postal Race (Friday)
15$
Registration for the Going Postal Race Friday for out of towners (and locals if you want!) Prizes and party at West Town Bikes to follow!
Valid for one month
- Registration for Friday's Going Postal Race!
Just Messenger Prom!
10$
Access to the coolest party for Messengers of 2026, featuring DJ Billy the Kid and Azuara, Sikmetra, and Glad! Music, Games, photobooth, and more!
Valid for one month
- Ticket to Messenger Prom
Just T-Shirt
20$
100% Cotten Gilden Limited Edition Chicago Courier Classic T Shirt!
Valid for one month
- CCC T Shirt

May 22nd

5:30pm Going Postal Race

Meetup:

THE INFAMOUS MESSENGER ALLEY across from 440 N. Orleans Petco.

Race for Out of Towners (locals can race too). 5:30pm Meet, 6:00pm start!

8:00pm First Night After Party

Meetup:

West Town Bikes (Ciclo Urbano) 2459 W Division

Social event at one of Chicoago's coolest local friendly bike shops in Humboldt Park!

Meet everybody and get acquainted with your fellow Bike lovers and Mess Heads before racing them the next day.

Free drinks provided by @Pint_Peddler on Instagram!!!

May 23rd

10:30am Chicago Courier Classic!

Meetup:

Eckhart Park (Noble and Chicago Ave.) Noble Square 10:30am Meetup

Race at 12:00pm Sharp! Approximately 3-5 hours! Bring your gear, patches, wrenches, tire levers, you never know what could happen! Winners will receive a plethora of prizes provided by our generous sponsors!

6:00pm Messenger Prom!

Meetup:

Not Not DIY Venue (West Humboldt, ask a punk for addy)

A full on Prom for messengers and their friends! Featuring live performances by SIKMETRA and GLAD, DJs AZUARA and BILLY THE KID!!

Messenger Games provided by @Ratpatrol, Prizes to be handed out, the mess prom king and queen to be selected! We're so excited for this one so don't miss out on this epic party!