Dairyland Dare

Set in southwest Wisconsin, the land left untouched by glacial flattening during the last ice age, the Dairyland Dare offers some of the most extreme hills in the Midwest. The area is characterized by steep, forested ridges, and deeply carved river valleys.

Pick from 4 one day challenges: 50K, 100K, 150K, or 200K. We welcome road and tri-bikes alike. E-bikes are welcome as well, but must follow the timeline accordingly (Click here to view FAQ page.) Scheduled five weeks prior to Ironman WI, the Dairyland Dare makes a great, last long ride before starting your Ironman taper.

Riders will climb through the historic streets of Mineral Point, WI and across the scenic countryside of Iowa County (WI) along their quest to cover distances of 50km to 200km before the sun goes down. Many of Wisconsin's steepest climbs are located throughout this region. With an abundance of community volunteers, ride support is second to none. Rest stops are well staffed and very well stocked with more food and sport drink than you could possibly consume. On course support is ever present and mechanical support is provided at every rest stop.

Afterwards join us at the post-ride party and enjoy music, laughs, and a meal that won’t leave you hungry! Register early to guarantee a spot in this great ride!