Cycling Events for an Active City Escape

By Kyle Goodman
Staff Writer

After a week of work, a weekend away from the bustle of the city is refreshing. Grab your bike and head for the open road. These eight cycling events will get you exploring beautiful landscapes with plenty of celebrations after your ride.


Ride for the ArtsMilwaukee

Love your bike and the arts? This ride in Milwaukee has something for the whole family. Distances span from the youth-friendly 5-mile route to the 70-mile challenge route with plenty in between. The 25-mile and up routes will travel over the iconic Hoan Bridge. Do not miss the after-party at the Summerfest grounds where there will be food, beer and entertainment.

Fat Tire TourMilwaukee

Billed as the oldest and most historic group ride in the greater Milwaukee area, this tour starts at the Historic Pabst Brewery in downtown Milwaukee. From there you will embark on a day of mystery stops with plenty of costumes, brews and fun along the way. You’ll cover 15 to 25 miles over 6 to 7 hours, creating a unique and unforgettable experience.

South Central

Horribly Hilly HundredsBlue Mounds

Once dubbed “Sufferfest of the Year!”, this one day cycling challenge is not for the faint of heart. Featuring 100k, 150k and 200k courses and 5,700 to 10,700 feet of elevation gain, riders will be challenged as they take in the scenery. Finishers will be treated to a traditional Wisconsin feast featuring locally-sourced hamburgers, chicken sandwiches, lotsa Wisconsin cheese and beer from Wisconsin Brewing Company.

Best Dam Bike RideWaukesha, Whitewater, Madison

Ready for the ride of a lifetime? On this ride, you’ll travel from Pewaukee to Madison with an overnight stay in Whitewater, joining fellow cyclists to beat MS. With multiple route options each day, you’ll experience an incredible level of camaraderie and accomplishment. Join as an individual or get a team together for this fully supported event for a great cause.

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Tyranena OktoberfestLake Mills

Celebrate your Oktoberfest with your bike, brews and support a local charity! Starting at Tyranena Brewing Company, your choices are 25, 55 and 75 miles with sag support and rest areas to help you through the ride. Once the ride is done, the celebrations begin. With three live bands, free tours of the brewery and a complete dinner, you’ll be saying “Prost!” all day.


Chippewa Valley CenturyChippewa Falls

Any ride sponsored by Leinenkugel’s is bound to be a good time. With 35, 50, 75 or 100-mile routes, this ride provides everything you need out on the road including rest stops with food & water, as well as a sag wagon. After you complete your ride, celebrate with a traditional Wisconsin brat feed with your fellow cyclists.

La Crosse Area Bicycle FestivalLa Crosse

Get away for Labor Day and enjoy two-wheeled bliss through the scenic valleys of the Mississippi River. This weekend-long event is free to the public with route information and turn-by-turn guides provided for you. After your ride, enjoy all La Crosse has to offer, and if you’ve got the legs for it, a hike up Grandad Bluff.


Get out and take a spin on your bicycle this summer. Even if there’s not an event going on, Wisconsin is home to a number of bike-friendly communities. And we’re proud of it!

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