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Cycling Found In Illinois

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Cycling Found in Illinois 2025 - 2026

Illinois is a brilliant place to take on a Gran Fondo. Find the perfect event for you with our comprehensive listings of bike races in Illinois 2025 - 2026. Whatever terrain you’re after you can find it in the Prairie State. Try out an urban event in Chicago or head out to rolling hills to experience some of the best cycling that Illinois has to offer. The term Gran Fondo is taken from Italian and roughly translates to ‘big ride’. With some events up to 300 miles long the name is pretty apt. Although don’t be put off most events have much shorter routes on offer too. Whether you’re a newcomer to riding and taking on your longest ride yet, or an experienced cyclist wanting to push yourself in a large group, a Gran Fondo will have the perfect challenge for you. Check out our exhaustive 2025 - 2026 Illinois Gran Fondos calendar list below, and use our month, distance and terrain filters to find your next challenge.

Race Calendar: Cycling Found In Illinois

🚀Boosted

Sweet Ride | Bike • Run • Walk

Willow Springs, Illinois
04 Oct 25
$32.80 - $54.00
🚀Boosted

Site M: Redacted

Chandlerville, Illinois
11 Oct 25
Free - $52.00
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2025 9th Annual Gold Star 500

Springfield, Illinois
31 May 25 - 27 Sep 25
Free - $450.00

SuperPrestige Cyclocross Series

Alton, Illinois
07 Sep 25 - 21 Sep 25
Free - $44.20

Capital City Century

Sherman, Illinois
13 Sep 25
Free - $67.45

2025 Kickapoo Endurance Race

Oakwood, Illinois
20 Sep 25 - 21 Sep 25
Free - $43.40

Tour De Charleston

Charleston, Illinois
27 Sep 25
$6.65 - $54.35

Sweet Ride | Bike • Run • Walk

Willow Springs, Illinois
04 Oct 25
$32.80 - $54.00

Trail Mix Off-Road Duathlon and Mountain Bike Race

Rockford, Illinois
05 Oct 25
Free - $85.80

Site M: Redacted

Chandlerville, Illinois
11 Oct 25
Free - $52.00

The Great Bottlecap Bike Race

Carlyle, Illinois
13 Sep 25
$38.10

Chicago Rides FAR

Warrenville, Illinois
27 Sep 25
Free

Pedalpalooza

Crystal Lake, Illinois
16 May 26 - 17 May 26
$16.90 - $27.50

Freedom Bike Ride

Chicago, Illinois
13 Jun 26 - 19 Jun 26
Free
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