Cycling Index

An index of cycling related events, groups, rides, races, and more in Northern Illinois.

Check before you register or travel: this calendar is compiled largely from organizer websites, and not every date has been verified by a human. Dates also move. Confirm directly with the organizer — and please send corrections or missing events to ryan@nicyc.com.

EventLocationDateType
Annual Velodrome 4k TTNorthbrook, IL8/8/2026Track
Little AppleManhattan, IL8/8/2026Gravel
Monsters of the Midway Criterium (Illinois Cup) CANCELLEDChicago, IL8/8/2026Criterium
Night Owl Bike RideCrystal Lake, IL8/8/2026Road/General
Double Bong 20-40 km TTKansasville, WI8/9/2026TT
Paul Douglas Pursuit CAMBrHoffman Estates, IL8/9/2026Mountain/Fat Bike
Rotary RideNaperville, IL8/9/2026Road/General
core4Iowa City, IA8/14/2026Gravel
Fast FittyCharlotte, MI8/15/2026Gravel
TreadfestLake Geneva, WI8/15/2026Mountain/Fat Bike
10 Mile TT National ChampionshipMaple Park, IL8/16/2026TT
Race the LakeFond du Lac, WI8/16/2026Road/General
Ride Across WisconsinEau Claire, WI8/22/2026Road/General
Chicago TriathlonChicago, IL8/22/2026Tri
The Coon Fork 40Augusta, WI8/22/2026Gravel
Tri-State Tour Chicago Century #2Tri-State, IL/WI/IN8/22/2026Road/General
Palos MeltdownPalos Park, IL8/23/2026Mountain/Fat Bike
Battle of CamRockCambridge, WI8/29/2026Mountain/Fat Bike
Boone County Road RaceBelvidere, IL8/30/2026Road/General
Return to Cherry Valley 20k Time TrialCherry Valley, IL8/30/2026TT
Wisconsin Masters Games – Road RaceMilwaukee, WI9/1/2026Road/General
Wisconsin Masters Games – TTMilwaukee, WI9/2/2026TT
Bike the DriveChicago, IL9/6/2026Road/General
Dust at DuskOregon, IL9/6/2026Gravel
Fall Fling Stage 3St Anne, IL9/12/2026TT
USA Cycling Gravel National ChampionshipsLa Crescent, MN9/12/2026Gravel
70.3 WisconsinMadison, WI9/12/2026Tri
Fall Fling Road TTSt Anne, IL9/13/2026TT
Relay CrossChicago, IL9/13/2026Cyclocross
Ironman WisconsinMadison, WI9/13/2026Tri
Dirtworx MTB FestFindlay, IL9/18/2026Mountain/Fat Bike
Chequamegon 40Cable, WI9/19/2026Mountain/Fat Bike
North Shore CenturyEvanston, IL9/20/2026Road/General
Bike the BarnsVerona, WI9/20/2026Road/General
CCC - Big MarshChicago, IL9/20/2026Cyclocross
CCC - Glenwood Academy (Sat)Glenwood, IL9/26/2026Cyclocross
CCC - Glenwood Academy (Sun)Glenwood, IL9/27/2026Cyclocross
Fall Fling Stage 1Wood Dale, ILSeptemberCriterium
Fall Fling Stage 2Wood Dale, ILSeptemberCriterium
Cycle On 2ndRockford, ILSeptemberRoad/General
Fall Color FestivalWhitewater, WISeptemberMountain/Fat Bike
Fontana TriathlonFontana, WISeptemberTri
Harmon 100Wauconda, ILSeptemberRoad/General
Heartland TourGeneseo, ILSeptemberRoad/General
Shaw Crank Redemption 20k Gravel TTManteno, ILSeptemberTT
Sun Prairie CupSun Prairie, WISeptemberCyclocross
Tour of Scenic Ogle CountyOregon, ILSeptemberRoad/General
Trail Mix Off-road DuathlonRockford, ILSeptemberTri
WICX – Field of RichesRichfield, WI10/3/2026Cyclocross
Driftless DaggerGalena, IL10/3/2026Gravel
Lead Ore GravelGalena, IL10/3/2026Gravel
Will to BenPort Byron, IL10/3/2026Road/General
WICX – Badger Prairie CXVerona, WI10/4/2026Cyclocross
CCC - Lords Park CXElgin, IL10/4/2026Cyclocross
WICX – Battle of WaterlooWaterloo, WI10/18/2026Cyclocross
Spotted Horse Gravel UltraSt Charles, IA10/19/2026Gravel
CCC - ABD Sycamore SpeedwayMaple Park, IL10/25/2026Cyclocross
Turkey BurnerNew Liberty, IA10/31/2026Gravel
Filthy 50Lanesboro, MNOctoberGravel
IRONBULL - Red Granite GrinderWausau, WIOctoberGravel
CCC - Campton CrossCampton Hills, IL11/1/2026Cyclocross
CCC - Groundhog PSI-clocross (Sat)Woodstock, IL11/7/2026Cyclocross
CCC - Groundhog PSI-clocross (Sun)Woodstock, IL11/8/2026Cyclocross
WICX – WI State ChampionshipWaterloo, WI11/21/2026Cyclocross
CCC - Quarry Cross The ForgeLemont, IL11/22/2026Cyclocross
Hugh Jass Bike RaceLake Geneva, WINovemberMountain/Fat Bike
CCC - Montrose BeachChicago, IL12/6/2026Cyclocross
Hugh Jass Bike RaceWaterloo, WIDecemberMountain/Fat Bike