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.