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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

SuperPrestige Cyclocross Series

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

Dirty Petersburg Gravel Ride

Petersburg, Illinois
Sun 15 Nov 26
Free
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2026 10th Annual Gold Star 500

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

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
$67.45

Richmond Rampage

Richmond, Illinois
Sun 20 Sep 26
$49.99 - $89.99

Sweet Ride | Bike • Run • Walk

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

Trail Mix

Rockford, Illinois
Sun 04 Oct 26
Free - $85.80

Dirty Petersburg Gravel Ride

Petersburg, Illinois
Sun 15 Nov 26
Free

Walk & Roll Chicago

Chicago, Illinois
Sat 05 Jun 27
Free - $38.10

Chicago Rides FAR

Northbrook, Illinois
Sat 26 Sep 26
Free

Site M: Redacted

Chandlerville, Illinois
Sat 03 Oct 26
Free - $52.00

White Squirrel Roubaix

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

Freedom Bike Ride

Chicago, Illinois
Sat 12 Jun 27 - Fri 18 Jun 27
Free
Showing 1-12 of 12 results

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