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  • About Us

    About Us

Dairyland Dare History

The Dairyland Dare, also previously known as the Wisconsin Dairyland Dare Cycling Challenge, was conceived and created by Stewart Schilling and Michelle Godez, avid cyclists from Southwest Wisconsin. The first ride took place in August 2006 and drew over 400 riders and offered three distances: 100K, 200K, and 300K. The ride doubled in size by 2007 and in 2008 two more distances were offered: 133K and 266K. By 2010 the ride grew to over 1000 riders and the distances that were offered expanded to: 50K, 100K, 150K, 200K, 250K, and 300K with very little overlap. This was the first year the ride included Mineral Point and Governor Dodge State Park. 2011 was the first year where Dairyland Dare was the final stage in the Wisconsin Triple Crown.

The ride embraced several themes over the years such as; the wild west; Dare Devil, paying homage to Evel Kneivel; Gran Fondo, with an early twentieth century Italian advertising; and an artistic theme from French Art Nouveau.

The event was purchased in 2015 by SyklusSport, LLC and held ownership until 2018. The ride did not take place in 2019 and was then purchased by Race Day Events. The event was cancelled in 2020 due to COVID-19. The distances now offered by the ride are 50K, 100K, 150K, and 200K.

Dairyland Dare History

About Race Day Events

Dairyland Dare is produced by Race Day Events. Race Day Events works with all types of events from small, community 5k/10K run/walks, to large multi-day bike rides, triathlons, and full marathons. Their goal is to put the participant first by creating accurate and well supported courses that are safe and fun. Their experienced staff strives to distinguish their events and host satisfying, innovative, recreational experiences.

About Race Day Events

Meet Your Ride Director

Brad Brad joined Race Day Events in June of 2022 but has been in the event industry since 2008. He’s originally from Lake Mills, IA where he grew up on a farm in the middle of nowhere but recently moved to Sun Prairie from Chicago where he spent the last 14 years producing mass participation running events. His favorite team is the Minnesota Vikings, but to distract from that he quickly mentions how he worked for the Packers one summer in high school and got to play catch with Brett Favre. In his free time Brad enjoys spending time with his wife, son and dog doing various outdoor activities.

Meet Your Ride Director