How many cycling events are coming up in Wisconsin?
Wisconsin has 2 upcoming events listed, from Sat, June 19, 2027 through Sat, June 19, 2027. The next one is Horribly Hilly Hundreds in Blue Mounds.
Wisconsin · Ride calendar
Cycling Events in Wisconsin
Wisconsin’s secret is the Driftless Area, an unglaciated corner in the southwest where the land folds into steep ridges and river coulees, laced with quiet gravel and some of the best backroad riding in the Midwest.
Elsewhere it’s rolling dairy country and Great Lakes shoreline, friendly and low-traffic. Summer is short and lush, winter is long and serious, and locals meet it head-on with fat bikes on frozen trails rather than giving the season up.
2 upcoming events · 1 road · 1 organized rides
By the numbers
Standouts in the State
The Wisconsin events that stand out on the numbers alone: the soonest start, the lowest listed entry, and the most route options.
Rides by City in Wisconsin
Soonest Rides in Wisconsin
2 totalHow 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 Wisconsin
What does it cost to enter a ride in Wisconsin?
Listed entry fees currently run from $38 to $120, depending on the event and route. Check each registration page for current fees and deadlines.
What kinds of rides are on the Wisconsin calendar?
The current listings break down as 1 road, 1 organized rides (events can carry more than one format on the day).
Riding Somewhere Else?
Every state, every event, or a straight search by name and city.