How many cycling events are coming up in Illinois?
Illinois has 9 upcoming events listed, from Sat, August 22, 2026 through Sat, October 3, 2026. The next one is KMC Sage City Classic in Monticello.
Illinois · Ride calendar
Cycling Events in Illinois
Illinois is prairie riding, flat and open, laid out on a farm-road grid that runs arrow-straight to the horizon. Chicago anchors the north with a long lakefront path and a real city cycling culture pressed up against Lake Michigan.
The wind is the terrain here. With nothing to block it, a crosswind will school you, and a headwind out is a tailwind you have to earn first. Pick your direction with the forecast.
9 upcoming events · 3 road · 1 gravel · 1 cyclocross · 4 organized rides
By the numbers
Standouts in the State
The Illinois events that stand out on the numbers alone: the soonest start, the lowest listed entry, and the most route options.
Rides by City in Illinois
Soonest Rides in Illinois
9 total Sat, August 22, 2026 KMC Sage City Classic Monticello, IL From $60 View Event Sun, August 30, 2026 Hope Echoes on the River Charity Bike Ride Geneva, IL From $125 View Event Sun, August 30, 2026 Illinois & Wisconsin Road Race State Championship - Boone County Road Race Belvidere, IL From $59.99 View Event Sat, September 12, 2026 HMFA’s Tour de Heartland Fundraiser Greenview, IL From $35 View Event Sun, September 13, 2026 SuperPrestige Cyclocross Series Alton, IL Free entry listed View Event Sat, September 19, 2026 Capital City Century Sherman, IL From $55 View Event Sun, September 20, 2026 Richmond Rampage Richmond, IL From $39.99 View Event Sat, October 3, 2026 Site M: Redacted Chandlerville, IL Free entry listed View Event Sat, October 3, 2026 Sweet Ride | Bike • Run • Walk Willow Springs, IL From $30 View Event
How we build these listings: Event counts, dates, and fees are computed from live registration listings (synced nationally from the RunSignup/BikeSignup platform), deduplicated and filtered to cycling disciplines. We list what is verifiably open for registration — not every ride that exists. Last updated July 19, 2026.
Common Questions About Riding in Illinois
What does it cost to enter a ride in Illinois?
Listed entry fees currently run from $0 to $125, depending on the event and route. Check each registration page for current fees and deadlines.
What kinds of rides are on the Illinois calendar?
The current listings break down as 3 road, 1 gravel, 1 cyclocross, 4 organized rides (events can carry more than one format on the day).
When is the busiest month for cycling events in Illinois?
September 2026 is currently the busiest month on the Illinois calendar with 4 listed events.
Riding Somewhere Else?
Every state, every event, or a straight search by name and city.