The 10 Best Cycling Events in Wisconsin!

Cycling races provide a great way to get some exercise, raise money for charities, and bring the community together. There are a number of races across the state of Wisconsin. From rides that benefit performing arts, to fat tire tours, to some of the toughest races in the Midwest, take your pick! Check out when and where our 10 best cycling races in Wisconsin are. 

1. Ride of the Arts

Starting in 1981, is the UPAF Ride of the Arts, which travels around Lake Michigan and South Milwaukee has around 4,000 participant riders. With beautiful views and a great cause of raising money for the performing arts the Ride of the Art’s is a great race. There’s a free post race party with food and Coors sampling.

2. Door County Century Ride

Courses vary in lengths of 28.5, 50, 70, or 100 miles—the cycling race encourages rider to bike at their own pace. After the race, participants can enjoy an Italian picnic dinner and a couple celebratory beers. The Door County Century Ride squeals off in mid September in gorgeous Door County.

3. Tyranena Oktoberfest Ride, Lake Mills, WI

Tyranena Oktoberfest Ride is celebrating 14 years as a fun charitable bike race.  The completion begins and ends at Tryanena Brewing Company in Lake Mills, Wisconsin. Riders can enjoy a free brewery tour, live music, drink tickets, t-shirt, and dinner after finishing their 25, 55, or 75-mile race.

4. Peninsula Century Fall Challenge

Peninsula Century Fall Challenge is a sister race of the Door County Century Ride. Participants of all levels are encouraged to choose from their 100, 62, 50, or 25-mile routes. The race was mapped out by experienced cyclists giving it an edge on other competitions in the area. After finishing the race there’s a celebratory party at Door County Brewing Company for beer, music, and food.

5. The Paperfest Tour de Fest, Appleton, WI

The Paperfest Tour de Fest supports Prevent Suicide Fox Cities in Appleton in the attempt to decrease the number of suicides and the toll on the survivors.  Routes of 18, 40, 70, or 100 are available and food and drinks are offered at pit stops throughout the race.  

6. Gourmet Bike Tour, Neenah, WI

For 31 years the Best Friends of Neenah-Menasha, a youth serving organization, has hosted the Gourmet Bike Tour rides through Neenah. The race has the options of choosing between the 4-12 miles, 25, 55, 75, or 100-mile course routes. T-shirts, food, and drinks are provided upon completion and throughout the race. Best Friends of Neenah-Menasha is a youth serving organization. 

7. Best Dam Bike Ride, Milwaukee, WI

This two day cycling race rides from Milwaukee to Madison with an overnight stay in Whitewater, Wisconsin. Feel the camaraderie as your bond with other riders over the same passion as you. Rest stops are every 10-12 miles with a fully staffed unit of medical personnel and law enforcement.

8. Pedal the Kettle, Waukesha, WI

The Spring City Spinners Club sponsors the Pedal Kettle every fall for the past 25 years. The race starts in Waukesha and offers various course lengths in a loop. All funds raised at the event go to other local bike related organizations.

9. Fat Tire Tour

The Fat Tire Tour started in 1996 in Lake Geneva. Today it is approximately 21.5 miles in distance and participants are encouraged to pedal at their own pace.  Bikers will travel through Lake Geneva, Fontana, and William’s Bay—not to mention the jaw dropping views of both Geneva and Como Lake.

10. Horribly Hilly Hundreds, Blue Mounds, WI

The Horribly Hilly Hundreds is one of the Midwest’s toughest mapped out cycling courses. The course acquired over 10,000 feet of elevation—speaking volumes to their race’s name. The nearly 1,300 participants get to finish their day with local food and drink. 

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