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.

2 upcoming events · more across Wisconsin

RoadGravelGran FondoCyclocrossOrganized RidesCharity Rides
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By the numbers

Standouts in Town

The Madison events that stand out on the numbers alone: the soonest start, the lowest listed entry, and the most route options.

Soonest startSep 27Badger ChallengeMadison, WILowest listed entry$38Loop the Lake - A bike ride to benefit our lakesMadison, WIMost route options6 routesBadger ChallengeMadison, WIFurthest outJun 19Loop the Lake - A bike ride to benefit our lakesMadison, WI
Sun, September 27, 2026 Badger Challenge Madison, WI 100 Miles100K50K25K From $45 View Event Sat, June 19, 2027 Loop the Lake - A bike ride to benefit our lakes Madison, WI From $38 View Event

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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 →
Bicycle Federation of Wisconsin Black Saddle Bike Shop Budget Bicycle Center - Repairs & Bicycle Accessories Budget Bicycle Center - Used Bicycles and Museum Crazy Lenny's E-Bikes Cronometro

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

How many cycling events are coming up in Madison, WI?

Madison, WI has 2 upcoming events listed, from Sun, September 27, 2026 through Sat, June 19, 2027. The next one is Badger Challenge in Madison.

What does it cost to enter a ride in Madison, WI?

Listed entry fees currently run from $38 to $45, depending on the event and route. Check each registration page for current fees and deadlines.

When is the busiest month for cycling events in Madison, WI?

September 2026 is currently the busiest month on the Madison, WI calendar with 1 listed event.