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Horribly Hilly Hundreds 2025

June 14, 2025

Updated July 5, 2024 --

The 2025 event date is not confirmed -- The Horribly Hilly Hundreds 2025 is the Midwest’s premiere sufferfest and is worth putting on your season's bucket list. Chosen as a Strambecco-rated best road cycling event in the Midwest and one of the Best Cycling Race Events in Wisconsin. The event has three ride options: 100k, 150k, and 200k routes; this event is no joke whatsoever. And with more than 10,000 feet of climbing, the Horribly Hilly Hundred is one of the hardest one-day events in the Midwest. With a massive rider field coming to the event in the past few years, the average field size for the ride is more than 1,300. A lottery system has been implemented to accommodate the mass number of sufferers to ride along Wisconsin’s scenic byways so everybody can have a fair chance at entry. For the people who want to go uphill a lot and test themselves physically and mentally, then the Horribly Hilly Hundreds is something to put on the bucket list.

The event producer for the Horribly Hilly is Race Day Events, founded in 2006, and is the Midwest's Event production leader. Specializing in endurance events, Race Day Events produces, manages, and assists with more than 300 events each year. From small 5Ks to IRONMAN and from Taste of Madison to local block parties, the Race Day Events team does it all in the greater Madison region.

Event & Course Info

The Horribly Hilly Hundreds offers three challenging courses for cyclists. The 200K option is a grueling ride covering 124.2 miles, with 40 significant climbs ranging from 50-foot bumps to a final 910-foot ascent, accumulating a total elevation gain of 10,700 feet. Riders on this route will find four full-service rest stops with bathrooms at mile markers 24, 44, 65, and 98, as well as at the finish line. Additionally, mini-water stops offering water and snacks will be available at critical intersections, though these will not have restrooms. Leg C of the 200K is noted as the easiest, providing some respite before the more demanding legs D and E.

The 150K route features 9,300 feet of elevation gain over its course. Full-service rest stops are strategically placed at mile markers 24, 51, 75, and at the finish line to ensure riders are well-supported throughout their journey. Meanwhile, the 100K course, which spans 66.5 miles, presents 5,700 feet of elevation gain. This route includes full-service rest stops at mile markers 24, 42, and at the finish line.

For all courses, maps, cue sheets, and adhesive arrows on the road help participants stay on track. Support services include sag wagons, medical assistance, and repair trucks, with ham radio operators stationed along the course for additional safety. Riders are advised to bring extra tubes and spare parts, especially if using specialized equipment, and a minimum 27-tooth rear cassette is recommended. In case of serious emergencies, participants should use their cell phones or seek help at the nearest house to call 911.

The Horribly Hilly Hundreds cycling event is an important fundraiser for the Friends of Blue Mound State Park (FBMSP), which is a 501(c)(3) non-profit organization. Recently the FBMSP has provided all or significant funding for the new pool, mountain bike trail improvements, trail signage, campsite upgrades, solar panels, winter trail grooming equipment, and other park needs. Future funds will help continue mountain bike trail improvements, group campsite development, and repairs needed after last summer's heavy rains.

Area Accommodations & Things to Do

Blue Mounds is a small village located in the southwestern part of the state of Wisconsin in the United States. It is situated in Dane County and is about 25 miles west of the state capital, Madison.  The village is named after the nearby Blue Mound, which is a hill that rises to a height of 1,719 feet and is one of the highest points in southern Wisconsin. The area surrounding Blue Mounds is primarily rural and agricultural, with rolling hills and scenic vistas.

In terms of accommodations, there are several options available in and around Blue Mounds, including bed and breakfasts, cabins, and campgrounds. The village itself has a few small motels and inns, but visitors may prefer to stay in nearby towns like Mount Horeb or Verona, which offer more options for lodging and dining. The area is also popular for outdoor activities, including hiking, biking, and skiing, and there are several parks and nature preserves in the vicinity.

Related Events

Multi-sport athletes looking for other premier races and events in Wisconsin and the broader Midwest region can take a peek at all of our related Strambecco Best rated event guides:

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Blue Mounds, Wisconsin

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