Horribly Hilly Hundreds on Facebook The Toughest One-Day Challenge Ride in the Midwest
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Horribly Hilly Hundreds
  • THIS YEAR'S RIDE DATE: JUNE 14, 2014
  • The registration lottery is now CLOSED.
  • The selection process took place on Monday, February 10th.
  • Selection status notifications have been sent to all lottery registrants.
  • Need to TRANSFER a registration? Click HERE


Three routes, two county tours, one result: a painfully fun, must-do biking experience destined to find its way onto your calendar for years to come.

2012 marked the 10th anniversary of the Horribly Hilly Hundreds. Once voted the "Sufferfest of the Year" by Madison weekly newspaper Isthmus, "The Toughest One-Day Challenge Ride in the Midwest" is not to be missed by serious riders anywhere.


Since 2003, Horribly Hilly participants have enjoyed a day of riding that results in an awe-inspiring accumulation of 10,000 feet of elevation gain in the Driftless Area** of Wisconsin. Growing in popularity each year, the Horribly Hilly registration has moved to an annual lottery system to accommodate the swelling number of interested riders. A second and third route option beyond the original course were added in 2005 and 2011. How hard do you want to push it? Choose between the 100K, 150K, and 200K routes. The day is capped with a meal featuring quality local food and beer.

Approximately 1,300 riders test their mettle on southwestern Wisconsin's scenic byways each year in the Horribly Hilly. Join the ranks of an inspired community of riders for the premier cycling event in the Badger State and beyond.


** Driftless refers to the unglaciated areas of Wisconsin and Iowa from the last glacial period, occurring approximately 10,000 years ago. As a result, dramatic landscapes of repeated hills and valleys create the terrain for more than 100 miles. The hills are steep, limestone-based, and mostly wooded.


The Horribly Hilly Hundreds event welcomes Race Day Events, LLC, as the new management team in 2013. Race Day Events will build on the work of Shelby Retzlaff, HHH event director for many years. Under Retzlaff's dedication and direction, the HHH has grown to a nationally recognized event — thank you, Shelby! Race Day Events, LLC, an event production company based in Verona, Wisconsin, brings experience with several high-quality nationwide events and pledges to continue the tradition of excellence that surrounds the Horribly Hilly Hundreds event and "Biking Like a Viking!"



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