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    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

Under New Management

UNDER NEW MANAGEMENT! Race Day Events Acquires Dairyland Dare Assets

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.

Under New Management

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

Abbey has been with Race Day since October 2015 and has been in the event industry since 2011. She's originally from Grand Rapids, Michigan, but has lived throughout the country where she gained experience in event management. She now lives in Madison with her husband Joe and her Golden Retrievers, Denard and Maizey Blue. Her favorite sports team is the University of Michigan - GO BLUE! Abbey's hobbies include running, cycling, swimming and spending time with friends and family. Her favorite thing about Race Day Events is the great people she gets to work with every day, and putting in the hard work to see smiling faces at the finish line.

Meet Your Ride Director