Conquer the Midwest’s ultimate climbing challenge in Wisconsin’s Driftless Area.

The Horribly Hilly Hundreds is a legendary one-day cycling event happening June 14, 2025, in Wisconsin’s dramatic Driftless Area. Riders can choose from three route options (100K, 150K, or 200K), all packed with relentless hills and up to 10,000 feet of climbing. Designed as a true endurance test, the event supports the Friends of Blue Mound State Park and invites over 1,200 cyclists each year to experience some of the Midwest’s best (and toughest) riding.

Three route options: 100K, 150K, and 200K. The ride starts and finishes at Blue Mound State Park, the highest point in Southern Wisconsin, and traverses rolling, picturesque rural roads with over 40 significant climbs.

• Huge elevation gain and relentless climbing: a ‘sufferfest’ revered by cyclists
• Panoramic vistas of Wisconsin’s Driftless Area
• Finishers treated to a post-ride meal with local food and craft beer
• Ride supports trail maintenance and park preservation efforts