How many cycling events are coming up in Wisconsin?
Wisconsin has 13 upcoming events listed, from Sat, August 1, 2026 through Sat, June 19, 2027. The next one is Bike to the Beat with myTEAM TRIUMPH in Combined Locks.
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.
13 upcoming events · 2 road · 1 gran fondo · 9 organized rides · 1 charity 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
13 total Sat, August 1, 2026 Bike to the Beat with myTEAM TRIUMPH Combined Locks, WI Free entry listed View Event Sat, August 1, 2026 Dairyland Dare Presented by Incredible Bank Dodgeville, WI From $125 View Event Sat, August 1, 2026 Loon Ride at Mercer Bike Fest Mercer, WI From $55 View Event Sun, August 2, 2026 Audaxity Milwaukee, WI See details View Event Sat, August 8, 2026 Hustle S'more for Lions Camp Rosholt, WI Free entry listed View Event Sun, August 16, 2026 RIDE WAUSHARA Wild Rose, WI From $15 View Event Wed, August 19, 2026 Beyond Design Bike Tour Ixonia, WI Free entry listed View Event Sat, August 29, 2026 Big Bull Falls Grand Fondo Wausau, WI From $60 View Event Fri, September 18, 2026 ¡Pick Me Up at the Border! Fitchburg, WI From $20 View Event Mon, September 21, 2026 Team ONE Mile Green Bay, WI See details View Event Sun, September 27, 2026 Badger Challenge Madison, WI From $45 View Event Sat, June 19, 2027 Horribly Hilly Hundreds Blue Mounds, WI From $120 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 Wisconsin
What does it cost to enter a ride in Wisconsin?
Listed entry fees currently run from $0 to $125, depending on the event and route. 2 of the 13 listed events haven't published pricing yet — check the registration page for current fees.
What kinds of rides are on the Wisconsin calendar?
The current listings break down as 2 road, 1 gran fondo, 9 organized rides, 1 charity rides (events can carry more than one format on the day).
When is the busiest month for cycling events in Wisconsin?
August 2026 is currently the busiest month on the Wisconsin calendar with 8 listed events.
Riding Somewhere Else?
Every state, every event, or a straight search by name and city.