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Cycling Found In Illinois

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Cycling Found in Illinois 2026 - 2027

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 2026 - 2027. 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 2026 - 2027 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

White Squirrel Roubaix

Olney, Illinois
Sat 15 May 27
$34.80 - $61.30
🚀Boosted

Mud Sweat and Gears MTB Race

Hudson, Illinois
Sat 29 Aug 26
Free - $38.10
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2026 10th Annual Gold Star 500

Springfield, Illinois
Sat 30 May 26 - Sat 26 Sep 26
Free - $500.00

Mud Sweat and Gears MTB Race

Hudson, Illinois
Sat 29 Aug 26
Free - $38.10

Illinois & Wisconsin Road Race State Championship - Boone County Road Race

Belvidere, Illinois
Sun 30 Aug 26
$69.99

HMFA’s Tour de Heartland Fundraiser

Greenview, Illinois
Sat 12 Sep 26
$38.10 - $48.70

Kickapoo Triple Crown

Oakwood, Illinois
Sat 12 Sep 26
Free - $38.10

SuperPrestige Cyclocross Series

Alton, Illinois
Sun 13 Sep 26 - Sun 20 Sep 26
Free - $44.20

Capital City Century

Sherman, Illinois
Sat 19 Sep 26
$57.15

Richmond Rampage

Richmond, Illinois
Sun 20 Sep 26
$29.99 - $69.99

Site M: Redacted

Chandlerville, Illinois
Sat 03 Oct 26
Free - $52.00

Sweet Ride | Bike • Run • Walk

Willow Springs, Illinois
Sat 03 Oct 26
$32.80 - $54.00

Trail Mix

Rockford, Illinois
Sun 04 Oct 26
$54.00 - $85.80

Walk & Roll Chicago

Chicago, Illinois
Sat 05 Jun 27
Free - $38.10

Hope Echoes on the River Charity Bike Ride

Geneva, Illinois
Sun 30 Aug 26
$66.20 - $134.78

White Squirrel Roubaix

Olney, Illinois
Sat 15 May 27
$34.80 - $61.30
Showing 1-14 of 14 results

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