Bike Rides in Illinois

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Welcome to your calendar for the best organized cycling events near you. From Century Rides, Gran Fondos, and Charity Bike Rides, to Mountain Bike, or Ultra Distance.
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Celebrate Trails Day Bike Ride

MOKENA, Illinois, United States

25 Apr 2026

21st Fat & Skinny Tire Fest Countryside Tour & Century

Winona Lake, Indiana, United States

16 May 2026

Illini Weekend Getaway – The Champaign of Rides! powered by Bicycle Illinois

Urbana, Illinois, United States

Century, Gran Fondo, Half Century, Kids, Metric Century, Mountain Bike, Randonneuring, Recreational, Tour
30–31 May 2026

OLD WORLD WISCONSIN

MADISON , Wisconsin, United States

Recreational, Tour
6–12 Jun 2026

44th BCLC Ramble Ride

Twin Lakes, Wisconsin, United States

7 Jun 2026

2026 B&O Bicycle Tour

Brownsburg, IN

Tour
13 Jun 2026

GRABAAWR “The GReat Annual Bicycling Adventure Along the Wisconsin River” powered by Bike Wisconsin

Prairie du Chien, Wisconsin, United States

Camp, Century, Gran Fondo, Half Century, Kids, Metric Century, Mountain Bike, Randonneuring, Recreational, Tour
13–20 Jun 2026

Wisconsin Wanderlust Fully Supported Rail Trail Bike Tour

Milwaukee, WI, USA

Recreational, Tour
14–19 Jun 2026

Wisconsin Wanderlust Rail Trail Fully-Supported Bike Tour

Madison, WI

Recreational, Tour
14–19 Jun 2026

Ride Across Illinois (RAIL) North powered by Bicycle Illinois

Moline, Illinois, United States

Century, Gran Fondo, Half Century, Metric Century, Mountain Bike, Randonneuring, Recreational, Tour
21 Jun 2026

Ride Across Illinois (RAIL) South powered by Bicycle Illinois

St. Louis, Missouri, United States

Century, Gran Fondo, Half Century, Metric Century, Mountain Bike, Randonneuring, Recreational, Tour
27 Jun 2026

La Porte Triathlon

La Porte, Indiana, United States

Multisport, Time Trial
11 Jul 2026

Tri-State Tour Chicago Century #1 powered by Bicycle Illinois

Whiting, Indiana, United States

Century, Gran Fondo, Half Century, Kids, Metric Century, Mountain Bike, Randonneuring, Recreational, Tour
12 Jul 2026

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

Chicago, Illinois, United States

Camp, Century, Gran Fondo, Half Century, Kids, Metric Century, Mountain Bike, Randonneuring, Recreational, Tour
18 Jul 2026

Dust Bowl 100 presented by Zipp

Eminence, Indiana, United States

Century, Gravel Grinder, Metric Century
25 Jul 2026

RAGBRAI Transportation: End of RAGBRAI to Chicago powered by Bicycle Illinois

Dubuque, Iowa, United States

Camp, Century, Gran Fondo, Half Century, Kids, Metric Century, Mountain Bike, Randonneuring, Recreational, Tour
25 Jul 2026

Tri-State Tour Chicago Century #2 powered by Bicycle Illinois

Whiting, Indiana, United States

Century, Gran Fondo, Half Century, Kids, Metric Century, Mountain Bike, Randonneuring, Recreational, Tour
22 Aug 2026

Route 66 Ride powered by Bicycle Illinois

St. Louis, Missouri, United States

Camp, Century, Gran Fondo, Half Century, Kids, Metric Century, Mountain Bike, Randonneuring, Recreational, Tour
19–26 Sep 2026

Will to Ben powered by Bike Wisconsin

Port Byron, Illinois, United States

Camp, Century, Gran Fondo, Half Century, Kids, Metric Century, Mountain Bike, Randonneuring, Recreational, Tour
3–9 Oct 2026
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