How many cycling events are coming up in Madison, WI?
Madison, WI has 1 upcoming listed event: Loop the Lake - A bike ride to benefit our lakes in Madison on Sat, June 19, 2027.
Wisconsin · Ride calendar
Cycling Events in Madison, Wisconsin
Madison is one of the Midwest’s great cycling cities, wrapped around its lakes and laced with paths. Car-free trails like the Military Ridge head west toward the Driftless hills, the road scene is deep, and cyclocross is close to a civic obsession here.
Summers are lush and made for riding, winters are long and cold, and locals meet the snow with fat bikes and cross races rather than surrender. Between the trails, the lakes, and the Driftless gravel nearby, it rarely runs out of options.
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Bike Shops in Madison
The easiest way to a start line is a shop that knows your bike. These Madison shops are listed free — addresses, websites, and phone numbers included.
Browse all Madison bike shops →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 Madison
What does it cost to enter a ride in Madison, WI?
Listed entry fees currently start at $38. Check each registration page for current fees and deadlines.