Countdown to Race Day: August 15, 2020

Join us in 2020!

At Race Day Events, our #1 priority is keeping our athletes, volunteers and staff safe. With the new circumstances we have all been thrown into, we are doing our best to adapt and continue to produce safe and enjoyable events. This is a labor of love for us and a passion of both yours and ours. We look forward to the day we are back to normal. Until then, we will continue to work with local health departments, municipalities, and the state to responsibly put forth plans to best adapt to the changing guidelines. We will keep you informed and updated as we traverse this new “course” together. As always we are here to support your goals, dreams, and ambitions. We will get through this together. Can’t wait to see you at the START LINE!

Set in southwest Wisconsin, the land 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. Scheduled four weeks prior to Ironman WI, the Dairyland Dare makes a great last big 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 from 50km to 200km before the sun goes down. Many of Wisconsin's steepest climbs are located throughout this region. With an abundance of volunteers from around the community, our support is second to none. Rest stops are well staffed and very well stocked with more food and sport drink that you could possibly consume. On course support is ever present and mechanical support is provided at every rest stop.

Join us at the post-ride party and enjoy music, laughs and a meal that won’t leave you hungry!

UNDER NEW MANAGEMENT! Race Day Events Acquires Dairyland Dare Assets

Madison, WI – August 6, 2019 –
Race Day Events, a leading endurance event management company, announces the acquisition of all remaining assets of the Dairyland Dare ride after the former management
company was forced to cancel the 2019 event. The acquisition adds yet another event to the expansive list of popular endurance events on the Race Day Events calendar.

“We are honored to return Dairyland Dare back to its former glory. This event has a long history in Wisconsin and pulls riders from all over the Midwest,” said Abbey VanValkenburg, Director
of Project Management at Race Day Events. “The event challenges riders as they tour through the beautiful and rugged Driftless Area in Southwestern Wisconsin. “

Race Day Events is known for production of the popular Horribly Hilly Hundreds cycling event, an event owned by the Friends of Blue Mounds Park as well as the Fitchburg Festival of Speed which
features the Wisconsin Cycling Association State Criterium Championships as well as a 25-mile family ride and running races.

“Our team will rely on their wealth of knowledge and experience to bring this amazing event back to life,” said Ryan Griessmeyer, President of Race Day Events. “We are very excited for 2020!”

Join us in 2020!

We're back!

We're back!

Registration for the 2020 ride!

Event Info

Get all event information needed for the 2020 ride!


Check out the bike routes here!