The team at Strambecco rates the Best Cycling Events Wisconsin 2025 based on various factors, including reputation, route quality, location, rider feedback, and the event's or race's overall uniqueness. Strambecco does not list every event.  We strive to identify and review special and noteworthy events, spanning Road, Gravel, and Mountain Bike events and races.

Wisconsin, with its rolling hills, stunning landscapes, and passion for cycling, is home to several iconic cycling events that draw riders from near and far. Cyclists flock to the Badger State to challenge themselves on routes that wind through picturesque countryside. If we had to pick the best of Best Cycling Events Wisconsin 2025, here are three of Wisconsin's most iconic cycling events:

1. Horribly Hilly Hundreds:

• Location: Mount Horeb, Wisconsin
• Distance and Terrain: As the name suggests, the Horribly Hilly Hundreds lives up to its reputation as one of the most challenging rides in the Midwest. Riders can choose from various routes that range from 100 to 200 kilometers and traverse steep ascents and descents.
• Challenges: With relentless climbs and descents, this event is not for the faint of heart. Riders must conquer hills with names like "Horrifying Hill" and "Brutal Berg" while navigating winding, scenic roads.
• Why it's Iconic: The Horribly Hilly Hundreds are known for their stunning vistas, demanding terrain, and a sense of accomplishment that comes with conquering the tough climbs. The event's challenging nature and beautiful surroundings make it a favorite among serious cyclists.

2. Ironbull Red Granite Grinder:

• Location: Wausau, Wisconsin
• Distance and Terrain: The Ironbull Red Granite Grinder offers a range of distances, from 10 miles to a grueling 100 miles. Participants experience a mix of gravel and paved roads, passing through the scenic and rugged landscapes of central Wisconsin.
• Challenges: The gravel sections can be unpredictable, and riders must be prepared to tackle a variety of surfaces. The course's diversity and scenic beauty set it apart.
• Why it's Iconic: This event has gained a reputation for its stunning and remote course, friendly atmosphere, and challenging terrain. It provides a unique opportunity for riders to explore the hidden gems of central Wisconsin.

3. Chequamegon MTB Festival:

• Location: Hayward, Wisconsin
• Distance and Terrain: The Chequamegon MTB Festival is one of the most famous mountain bike races in the Midwest. The main event, the Chequamegon 40, covers 40 miles of beautiful Northwoods terrain, including forest trails and scenic lakeside paths.
• Challenges: While not as hilly as some other events, the rugged Northwoods trails present their own set of challenges, from rooty sections to sandy tracks.
• Why it's Iconic: The festival offers a unique blend of mountain biking, natural beauty, and a festival atmosphere. The camaraderie among riders and the idyllic Northwoods setting make it an unforgettable experience.

In conclusion, these iconic Wisconsin cycling events, along Strambecco's full list, offer riders a diverse range of challenges, from brutally hilly to gravel grinding and mountain biking. They celebrate the state's natural beauty and vibrant cycling community, making them must-attend experiences for cyclists of all levels. Whether you're a hardcore racer or a recreational rider, these events allow you to immerse yourself in the beauty and adventure that Wisconsin's cycling scene has to offer.

If you have suggestions on other events we should consider or review, please contact us here or send us a note at editors@strambecco.com.  Strambecco also rates Midwest's best Road, Gravel, and MTB events.