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
