Horribly Hilly Hundreds (HHH): The Ultimate Midwest "Suffer Fest"

Prepare to test your mettle against the most demanding terrain the Midwest has to offer. The 23rd Annual Horribly Hilly Hundreds is not just a ride; it is a badge of honor, a test of endurance, and a celebration of cycling grit in the breathtaking, steep, and scenic Driftless Area of southwestern Wisconsin.

Course Description: "Horribly" Hillier Than You Expect

Don't let the Wisconsin scenery fool you. While beautiful, this region is known for steep, relentless, and unforgiving terrain, with up to 10,000 feet of elevation gain. Riders will experience roughly 40 significant rises on the 200K route—ranging from short, punching 15–20% grade "bumps" to long, sustained, lung-busting climbs.

200 KM (124.2 miles): The full "Suffer Fest." Over 10,000+ ft of climbing.
150 KM (93.2 miles): A formidable, 9,300-ft challenge.
100 KM (62.1 miles): 5,700+ ft of elevation gain for a punchy, technical ride.

Note: Technical descents accompany the brutal climbs, requiring skilled bike handling and sharp brakes.

Event Highlights & Participant Details

Start Time: 6:45 AM CDT
The "Suffer Fest" Atmosphere: Renowned as the toughest one-day challenge in the Midwest, bringing together ~1,000+ serious riders for a,painfully fun experience.
Full Support & Sag: Four+ full-service, stocked rest stops featuring water, nutrition, and toilets. The event includes SAG wagons, mechanic support, and medical assistance to keep you moving.
Post-Ride Party: Celebrate your survival! The event concludes with a post-ride meal featuring local food and refreshing beer.
Swag & Perks: Registration includes a high-quality, event-specific gift (such as socks or a water bottle) and custom, color-coded route maps.
Charity Component: Ride for a cause. The event is the flagship fundraiser for the Friends of Blue Mound State Park.

Important Information

Register Early: This event consistently fills up months in advance, often moving to a lottery system due to extreme popularity.
Price Increases: Early bird pricing ends in early March.
Training Series: The Bombay Bicycle Club sponsors a 15-week early-season training series (BCETS) specifically designed to prepare riders for HHH.
Double Your Challenge: Combine your experience with the Driftless Double Dare - a special partnership with the Dairyland Dare - to earn a custom souvenir and serious bragging rights.

See Why the Horribly Hilly Hundreds is Considered the Hardest Ride in the Midwest

Frequently Asked Questions

What are the different route options for the Horribly Hilly Hundreds?

Riders can choose from three distance options tailored to different fitness levels and goals. The 100K, 150K, and 200K routes all traverse the same challenging terrain in the Driftless Area, allowing you to decide how much elevation gain and distance you want to tackle on race day.

How much elevation gain should I expect to climb?

The Horribly Hilly Hundreds features up to 10,000 feet of elevation gain across the event's routes. This makes it one of the toughest one-day challenges in the Midwest, so proper training and pacing strategy are essential for success.

How many riders typically participate in this event?

Approximately 1,200 serious cyclists test their mettle at the Horribly Hilly Hundreds each year. Registration reaches capacity months in advance, so interested riders are encouraged to register early to secure their spot in this premier Midwest cycling challenge.

What terrain and scenery can I expect in the Driftless Area?

The event takes place across southwestern Wisconsin's scenic byways in the Driftless Area, known for its steep, rolling hills and breathtaking landscapes. Two county tours are incorporated into the routes, offering competitive cyclists a true test of climbing strength and technical descending ability.

What happens after I finish the ride?

All finishers are invited to celebrate at a post-ride meal featuring quality local food and beer. This is a great opportunity to recover, connect with fellow riders, and enjoy the sense of accomplishment that comes from completing one of the Midwest's most demanding one-day challenges.

Is this event part of a competitive race series?

The Horribly Hilly Hundreds is a challenge ride and fundraiser for Friends of Blue Mound State Park rather than a traditional race with categories and podium ceremonies. However, serious competitive cyclists treat it as a crucial test of their endurance and climbing fitness.

What gear and bike setup should I use for this event?

Given the extreme elevation gain and hilly terrain, a road or gravel bike with a climbing-friendly gearing setup is recommended. Check the event website for the latest details on course conditions and any specific equipment recommendations for tackling the Driftless Area's demanding climbs and descents.

Wisconsin Cycling Events

Events in Wisconsin

USA Cycling Collegiate Road National Championships

Horribly Hilly Hundreds