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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

KMC Sage City Classic

Monticello, Illinois
Sat 22 Aug 26
$54.00
🚀Boosted

Cataylst XC

Makanda, Illinois
Sat 08 Aug 26
$27.50 - $54.00
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Sangamon Cycling Series - Four Ride Series

Springfield, Illinois
Sat 09 May 26 - Sat 08 Aug 26
$36.55

Thunder Road Gravel Tour

Springfield, Illinois
Sun 24 May 26 - Sun 09 Aug 26
Free

2026 10th Annual Gold Star 500

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

The Great Bottlecap Bike Race

Carlyle, Illinois
Sat 06 Jun 26
$38.10

Freedom Bike Ride

Chicago, Illinois
Sat 13 Jun 26 - Fri 19 Jun 26
Free

Tour De Charleston - 10th Annual

Charleston, Illinois
Sat 13 Jun 26
$43.75 - $64.95

56th Annual Swedish Days Ride

Sugar Grove, Illinois
Sun 14 Jun 26
$48.70

Ride Across Illinois (RAIL) North powered by Bicycle Illinois

Moline, Rock Island
Sun 21 Jun 26
Free

Trailnet I Scream for Ice Cream Ride

Edwardsville, Illinois
Sun 28 Jun 26
$11.60 - $43.40

RAGBRAI Transportation: Chicago to the Start of RAGBRAI powered by Bicycle Illinois

Chicago, Cook
Sat 18 Jul 26
Free

2026 CAMBr Chicagoland Race Series Powered by SRAM

Carpentersville-Hoffman Estates-Willow Springs, Illinois
Sun 26 Jul 26
Free - $48.70

Kevin D. Rice. Sr. Memorial Bike Ride and Picnic

Rockford, Illinois
Sat 01 Aug 26
$26.25 - $64.36

Cataylst XC

Makanda, Illinois
Sat 08 Aug 26
$27.50 - $54.00

KMC Sage City Classic

Monticello, Illinois
Sat 22 Aug 26
$54.00

Mud Sweat and Gears MTB Race

Hudson, Illinois
Sat 29 Aug 26
Free - $27.50

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

Belvidere, Illinois
Sun 30 Aug 26
$49.99

Hope Echoes on the River Charity Bike Ride

Geneva, Illinois
Sun 30 Aug 26
$134.78

HMFA’s Tour de Heartland Fundraiser

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

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
$19.99 - $49.99

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
Showing 1-23 of 23 results

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