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


2026 marks the 23rd Horribly Hilly Hundreds. Commonly referred to as the "Suffer fest of the Year" and "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, although not a lotter anymore the Horribly Hilly registration has reached capacity each year months prior to the event. 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 1,200 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.