Tag: bike races

August Bike Rides and Races in Chicagoland 

Below we highlighted some fun rides or races within a two-hour drive from Chicago (in light traffic, bleh) along with a comprehensive list of events in the table at the bottom. Thanks to Cycling Index – Northern Illinois Cycling for assembling this data.  

Looking for a bike shop near you that can get your bike ready for any of these events? Talk to the Tailwind crew to get your wheels in shape (round, ideally) or hit us up for fitting.  

If you’re looking for a regular weekly group ride, Tailwind sponsors the Half Acre Wednesday night group ride. It’s roughly 20 miles from Winnemac Park to the Half Acre brewery – and there’s a slow group or a fast group.

Highlighted Rides in Chicagoland

Annual Velodrome 4k Time Trial

• Date: Sunday, August 9, 2025 
• Type: Time trial – velodrome 
• Location: Northbrook, IL 
• Details & registration:https://www.wiilcycle.org/event/2nd-annual-velodrome-4k-tt/

Little Apple Gravel (20k-40k) Time Trial

• Date: Sunday, August 10, 2025 
• Type: Gravel TT 
• Location: Manhattan, IL 
• Details & registration:https://www.bikereg.com/littleapple

Palos Meltdown CAMBR 

• Date: Sunday, August 10, 2025 
• Type: MTB Race 
• Location: Palos MTB trails, IL 
• Details & registration: https://cambr.org/news_manager.php?page=24504

Tri-State Tour Chicago Century

• Date: Sunday, August 23, 2025 
• Type: Non-competitive entury ride (also non-century option) 
• Route: Whiting, IN → Kenosha, WI 
• Details & registration:Bicycle Illinois – Illinois’ Bicycle Touring Company

Return to Cherry Valley 20k Time Trial

• Date: Sunday, August 24, 2025 
• Type: Time trial (20k) 
• Location: Cherry Valley, IL 
• Details & registration:https://www.wiilcycle.org/event/return-to-cherry-valley-20k-tt/

Relay Cross Chicago

• Date: August (date TBD), 2025 
• Type: Cyclocross relay race 
• Location: Chicago, IL 
• Details & registration:Relay Cross – xXx Racing – Athletico

Chicago Triathlon

• Date: August 23-24, 2025 
• Type: Triathlon (includes cycling) 
• Location: Chicago, IL 
• Details & registration:Chicago Triathlon

Bike the Drive

• Date: Sunday, August 31, 2025 – 6:30 AM start 
• Type: Car-free city ride along Lake Shore Drive 
• Location: Grant Park (Butler Field), Chicago 
• Official site & registration: Active Transportation Alliance event info REGISTER – Bike the Drive

Event Summary Table

Event	Location	Date	Type
CowaLUNGa	Gurnee, IL	8/2/2025	Road/General
Bryce Master 19k TT	Harvard, IL	8/2/2025	TT (Time Trial)
Night Owl Bike Ride	Crystal Lake, IL	8/2/2025	Road/General
Illinois Road Race Championship	St. Anne, IL	8/3/2025	Road/General
Little Apple	Manhattan, IL	8/3/2025	Gravel
Naperville Sprint Triathlon	Naperville, IL	8/3/2025	Triathlon (Tri)
New Glarus Road Race	New Glarus, WI	August 2025	Road/General
Annual Velodrome 4k TT	Northbrook, IL	8/9/2025	TT (Time Trial)
Palos Meltdown	Palos Park, IL	8/10/2025	Mountain/Fat Bike
Double Bong 20–40 km TT	Kansasville, WI	8/10/2025	TT (Time Trial)
Rotary Ride	Naperville, IL	August 2025	Road/General
Ride Like An Egyptian	DeKalb, IL	August 2025	Road/General
Fast Fitty	Charlotte, MI	8/16/2025	Gravel
core4	Iowa City, IA	8/16/2025	Gravel
10 Mile TT National Championship	Maple Park, IL	8/17/2025	TT (Time Trial)
Race the Lake	Fond du Lac, WI	August 2025	Road/General
Ride Across Wisconsin	Southern, WI	August 2025	Road/General
The Coon Fork 40	Augusta, WI	8/23/2025	Gravel
Return to Cherry Valley 20k Time Trial	Cherry Valley, IL	8/24/2025	TT (Time Trial)
Tri-State Tour	Tri-State (IL/WI/IN)	August 2025	Road/General
Treadfest	Lake Geneva, WI	August 2025	Mountain/Fat Bike
Relay Cross	Chicago, IL	August 2025	Cyclocross
Chicago Triathlon	Chicago, IL	August 2025	Triathlon (Tri)
Fall Fling Stage 1	Wood Dale, IL	8/30/2025	Criterium
Fall Fling Stage 2	Wood Dale, IL	8/31/2025	Criterium

Chicago Bike Races and Rides in May

Here is a list of bike races in the Chicago area, plus things to do on a bike for May of 2025. Events are divided into races for competitive cycling, and rides for social outings or non-competitive endurance events (like brevets).

If you’re looking for a regular group ride, check out Half Acre Cycling’s group ride finder.

Races:

May 3: 1904 Gravel Race – Illinois City, IL

May 4: Harvard 33.3k Time Trial – Harvard, IL

May 6: Labagh Woods Ladies’ Night Crits – Chicago, IL

May 13: Labagh Woods Practice Crits – Chicago, IL

May 15: Thursday Night Track Racing – Northbrook, IL

May 18: Kankakee 20k Time Trial – Kankakee, IL

May 24: ABD Memorial Day Weekend Omnium #1 – Wood Dale, IL

May 25: ABD MDW Omnium #3 – Wood Dale, IL

May 25: Kane County Ten Mile Time Trial – Maple Park, IL

Rides

May 3: The Chicago Tweed Ride – Oak Park, IL

May 3: Barrington Boomerang 200k – Barrington, IL

May 4: Pastry-Bike-Pastry – North Aurora, IL

May 17: Pedalpalooza – Crystal Lake, IL

May 17: Chicago-Milwaukee-Chicago300k – Chicago, IL

May 18: Everybody Rides – St. Charles, IL

May 24: Blackhawk Country Roads – Rockford, IL

May 25: McHenry County Century – Lake in the Hills, IL

May 30: Chicago Critical Mass – Chicago, IL

May 31: Aurora City of Lights 400k – Aurora, IL

Pic from The Garden, Chicago’s north side bike jumping park.