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Tag: bike races

MARCH 2026 CYCLING EVENTS IN CHICAGOLAND

Ullr, the Norse god of winter, hung up his crampons and stowed his toboggan for the year, which means the thaw is officially underway, and for Chicago cyclists that means one thing: it’s time to trade the indoor trainer for the open road. From the social miles of Wauconda to the brutal gravel grind of the “Hell of the Wind,” March is packed with opportunities to test your legs and fortitude. Whether you’re looking for a high-speed criterium or a muddy post-season cyclocross challenge, here are the key events hitting the Midwest calendar this month.

St. Patrick’s Day Ride — March 15

https://wheelmen.com/st_pats.asp

This fun, social road and general ride takes place in Wauconda, IL, celebrating St. Patrick’s Day with cyclists of all levels. The ride is a community favorite that embraces the seasonal transition into spring and leverages festive energy for a group outing.

Hell Of The Wind — March 28

https://www.bigrivergravel.com/about-1

Held in New Liberty, IA, Hell Of The Wind is a challenging gravel ride that pushes participants over variable terrain typical of early spring gravel seasons. Riders can expect rougher roads, wind exposure, and a strong testing ground for the upcoming cycling calendar.

Melting Mann — March 28

https://meltingmann.com

The Melting Mann event in Vandalia, MI is a spring gravel ride designed to shake off winter rust. It tests riders’ endurance across melting terrain and often muddy conditions as routes loosen with warmer temperatures approaching.

Autobahn Omnium — March 28 – 29

https://www.bikereg.com/autobahn-omnium

The Autobahn Omnium in Joliet, IL is a criterium racing event where riders compete in high-speed circuits around a closed course. As part of the spring racing calendar, this event attracts both local and competitive racers seeking fast laps and tactical competition.

Return to the Hills CX — March 29

https://www.bikereg.com/return-to-the-hills

Return to the Hills Cyclocross in Rockford, IL can be seen as the earliest cyclocross race of the season, or the latest race of last season, or just a thing of its own. Either way, It’s an off-road challenge that combines grass, mud, and technical obstacles. If you didn’t get enough cyclocross during the Chicago Cross Cup, here’s a second chance at glory.

Great Lakes Rando — March (Date TBD)

https://glr.greatlakesrando.org/stats/pages/myClub.xhtml

The Great Lakes Rando in Barrington, IL is a long-distance randonneuring event where cyclists ride extended courses at their own pace. With routes that test endurance and navigation skills, this ride embraces the tradition of unsupported, self-paced cycling.

There’re more events to come, keep checking the site for updates!

2025 Cyclocross Service Package

Mud happens. We handle it. Gear up for the Chicago Cross Cup (CCC) with Tailwind’s all-in service package designed to keep your race bike fast, quiet, and ready every weekend.

What’s included for $270

  • Pre-season full tune-up to dial shifting, braking, and tire clearance.
  • One bike wash + lube between every race (that’s 9 clean/relube services across the series, plus mechanical tweaks).
  • Race-day mechanical support at the Tailwind tent for those last-minute adjustments.
  • Optional bike transport to the race—skip the rack and focus on your start.
  • Racing with a backup in the pit? We’ll act as your pit crew during the race.

Extra perks

  • 15% off parts for your race bike.
  • 20% off tubular gluing.
  • If a race is canceled, you’ll get shop credit for a clean & lube.

Ready to roll? Bring your bike in for the pre-season tune, lock in your spot for all 9 CCC rounds, and let us sweat the maintenance while you chase the holeshot.

Call or stop by Tailwind Cycles to sign up today.

Interested in Other Races?

In addition to the Cross Cup, the other big racing series in the area is the Wisconsin CX series.

For other rides and races in Chicagoland, check out the Northern Illinois Cycling Index.

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

EventLocationDateType
CowaLUNGaGurnee, IL 8/2/2025 Road/General 
Bryce Master 19k TTHarvard, IL 8/2/2025 TT (Time Trial) 
Night Owl Bike RideCrystal Lake, IL 8/2/2025 Road/General 
Illinois Road Race ChampionshipSt. Anne, IL 8/3/2025 Road/General 
Little AppleManhattan, IL 8/3/2025 Gravel 
Naperville Sprint TriathlonNaperville, IL 8/3/2025 Triathlon (Tri) 
New Glarus Road RaceNew Glarus, WI August 2025 Road/General 
Annual Velodrome 4k TTNorthbrook, IL 8/9/2025 TT (Time Trial) 
Palos MeltdownPalos Park, IL 8/10/2025 Mountain/Fat Bike 
Double Bong 20–40 km TTKansasville, WI 8/10/2025 TT (Time Trial) 
Rotary RideNaperville, IL August 2025 Road/General 
Ride Like An EgyptianDeKalb, IL August 2025 Road/General 
Fast FittyCharlotte, MI 8/16/2025 Gravel 
core4Iowa City, IA 8/16/2025 Gravel 
10 Mile TT National ChampionshipMaple Park, IL 8/17/2025 TT (Time Trial) 
Race the LakeFond du Lac, WI August 2025 Road/General 
Ride Across WisconsinSouthern, WI August 2025 Road/General 
The Coon Fork 40Augusta, WI 8/23/2025 Gravel 
Return to Cherry Valley 20k Time TrialCherry Valley, IL 8/24/2025 TT (Time Trial) 
Tri-State TourTri-State (IL/WI/IN) August 2025 Road/General 
TreadfestLake Geneva, WI August 2025 Mountain/Fat Bike 
Relay CrossChicago, IL August 2025 Cyclocross 
Chicago TriathlonChicago, IL August 2025 Triathlon (Tri) 
Fall Fling Stage 1Wood Dale, IL 8/30/2025 Criterium 
Fall Fling Stage 2Wood 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.


/TAILWINDCYCLES

Tailwind Cycles is a full-service bike shop located in Albany Park, Chicago offering in-shop and mobile bike repair, tune-ups, and bike fitting.


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