Within the Wisconsin bicycling community there is a debate about which one of the state’s three most popular and challenging bike rides is the most difficult. Last summer I rode the short routes of all three of these rides in an attempt to decide for myself which one is the most difficult.

The Horribly Hilly Hundreds (HHH) 100K route is 66 miles long with 5,700 feet of climbing. The Insane Terrain Challenge (ITC) 125K route is 78 miles long with 7,700 feet of climbing. The Dairyland Dare 100K route is 65 miles long with 5,200 feet of climbing. The rides are held about a month apart starting in June with the HHH and ending in August with the DLD. All three of these very hilly bike rides are located near each other in southwestern Wisconsin but share very few of the same roads.

I am quite familiar with the roads in this portion of Wisconsin, having had a big hand in determining the routes for the HHH and the ITC. But other than being familiar with the roads on the DLD, I had not ridden the exact route laid out by its organizers. I already had an opinion on whether the HHH was more difficult than the ITC, but I needed to ride the DLD so I could make a fair comparison.

I considered such ride elements as the number of major climbs, the difficulty of the last climb, the pacing of the climbs throughout the ride and the degree of difficulty of the climbs. In addition, I considered factors such as where each ride fell on the calendar, plus exposure to wind and sun.

After finishing the DLD 125K last August, I gathered all my notes and recollections and came to the conclusion that the HHH 100K was the most memorable and difficult. Most people would agree that all three rides are both beautiful and extremely challenging. But in my mind the 100K HHH route is a truly special ride.

The HHH 100K ride for me started with my cell phone alarm going off at 4:45 a.m. on June 20, 2009. I was apprehensive about what lay ahead of me that day despite having done this ride and many others like it numerous times. A perfect morning greeted me when I opened the door of my motel room. The sun on this, the longest day of the year, was already brightening the eastern horizon. The air was warm, the roads were dry, and the wind was calm. Suddenly, I was ready to ride.

As I drove south on County Road F from Mazomanie towards Blue Mound State Park through the fog filled valleys, the hilltops lay exposed and silhouetted against the brightening sky. Thoughts from past rides filled my head. I had vivid memories of riding every one of these roads. I saw hills I knew I would be climbing later in the day. Around 5:30 a.m. I arrived at the parking lot at the top of the Blue Mound. The start line was actually one mile below the parking lot in the little town of Blue Mounds.

Many riders had already arrived and some were even leaving before 7 a.m., probably to avoid the mass start. The sight of cars, bumper to bumper, entering the parking area and the sounds of bikes being unloaded and friends greeting one another gave me a real sense something special was about to happen. The popularity of this ride is truly amazing.

I started with a group of riders. I drifted towards the back of the pack to enjoy the colorful sight of the long line of riders ahead of me. The first big downhill on County Road K, north of Barneveld, brought everyone into Walnut Hollow at the base of Blue Mound. From here we climbed 620 feet up Mounds Park Road. I passed riders already walking their bikes up the steepest portion of this first real climb. How many of them knew that they would be climbing this one a second time at the end of the ride? Were many of them already wondering how they were going to respond to the challenge of the other 13 major hills ahead?

Familiarity with the climbs was very helpful to me. I knew when to shift into the appropriate gear at the right time, which allowed me to maintain my pedaling cadence and breathing. Many of the early climbs were shaded, which kept them cool and quiet. At times the only sounds I heard were derailleurs downshifting and the soft chatter between riders, as they encouraged each other.

I think riders are drawn to the HHH for the challenge of climbing. But for every uphill there is a corresponding big downhill. At the top of many hills there is a panoramic view of the Wisconsin countryside. No better view and downhill can be found on the HHH than those experienced on County F at Brigham County Park. The view to the north towards the Wisconsin River valley is inspiring. And the downhill, which follows shortly thereafter, may be the best descent in the state. Descending 760 feet over four miles can trick some riders into thinking the HHH isn’t so challenging a ride.

A right turn onto Blue Mounds Trail Road quickly brought back into focus the real test HHH presents. A climb up Sand Ridge started shortly after crossing Elvers Creek, rising 260 feet in the next three-quarters of a mile effectively taking back almost all of the altitude lost in the descent from Brigham County Park. Two high-speed descents and another long climb brought the ride out to State Highway 78, where a Dane County sheriff’s deputy was positioned to assist riders making the turn onto Union Valley Road.

I have climbed the increasingly difficult stepped hill on Union Valley Road many, many times and have always enjoyed it. To be on this shaded climb on a cool, sunny morning with dozens of other riders has always given me a big shot of adrenaline, which has helped me look forward to the upcoming trials.

The 1 1/2-mile stretch of riding on County Road KP after the Union Valley Road descent is the only truly flat section of road on the 100K route. I cannot think of any other ride where a flat section of road would be noteworthy.

The reality of the HHH is quickly reestablished with the steep climb on Schebel Road up to the first rest stop of the ride at Festge Park. There hundreds of riders seek relief, nourishment and friends from whom they had become separated.

One of the most notorious climbs on the HHH is encountered soon thereafter. I have for years called the last section of the hill on Barlow Road a wall. This section is just over a quarter-mile long, but in that distance it gains 240 feet with an average 13 percent grade. In the middle of this climb may be the point on the HHH where riders intending on completing the 200K route decide maybe 100K is enough. 200K riders who struggle badly on Barlow Road and on the next steep climb on Mineral Point Road are much more likely to get off the 200K route by continuing straight on County Road J instead of turning right onto Greenwald Road. At this point in the HHH there is only one steep climb on Zwettler Road to negotiate before Rest Stop No. 2 on County Road K.

This rest stop has become known as “the graveyard.” It is the last full service stop on the ride and also the point where the 200K and 100K routes rejoin each other. Many riders reaching this point are near exhaustion. I rolled into the rest stop to find bodies and bikes strewn across the ground. In order not to join them, I made a point to keep my elapsed time there as short as possible. It is certainly easier to linger than to get back on the road and face the most difficult series of hills on the ride.

Every rider leaving Rest Stop No. 2 has a very important decision to make before continuing. If they decide to finish the ride as they set out to do, they will have to endure three major climbs over the next 15 miles before encountering the final climb to the finish. If they elect to take the shortcut, they will still have to survive the final climb, but the finish is only 3 1/2 miles away. I elected to finish the 100K HHH route as designed.

The first major climb on the last portion of the HHH is sadistically 1 1/2 miles from the graveyard. I can make this statement because I helped put it there. It is not a good idea to undertake this climb on a full stomach with muscles that have cooled down from a long rest. Pinnacle Road ascends 310 feet in a half mile at a 12 percent pitch. I knew getting to the top was just the start of the hardest part of courses.

Yet to come were 400-foot, three-quarter-mile climbs on Lake View Road, with a maximum grade of 11 percent, and County Road T into Barneveld. Fortunately, there are also a couple of very fast downhills on good pavement on Knudson and Bryn Gyrwen roads between all uphills. The downhills are nice rewards. The two miles between Barneveld and the last downhill on Ridge View Road allows one to refocus in time to tackle the last difficult climb of the ride. Saving the biggest challenge of the ride for the end is devious but ultimately empowering.

When you turn onto Mounds Park Road after a short jog on County K from Ridge View Road, you can see the top of the Blue Mound looming on the horizon. Over the final 3.5 miles of HHH, 925 feet of elevation are gained. I believe this has to be the most difficult finish to any bike ride currently in existence in Wisconsin. When Mounds Park Road crosses Blue Mounds Creek, the grade increases to 11 percent and remains there for the next three-quarters of a mile. A short 55-foot descent breaks up the climbing just before the ride enters Blue Mound State Park. The last half-mile of the HHH ascends 300 feet at a 12 percent grade bringing you to the highest point in southern Wisconsin.

I finished the last climb feeling reasonably well. I had ridden all the roads of the HHH many times over the years. My experience on these roads certainly contributed to my success. But I witnessed plenty of other riders not enjoying the finish. In fact, I have never seen so many riders walking to the finish of a bike ride. Any questions about the difficulty of the HHH 100K are answered throughout the course, but the point is driven home most emphatically on that final climb.

Greg Krystek is a 60-year-old mechanical engineer living in Greenfield, Wisconsin, with his wife of 28 years, Denise. He and Denise still enjoy riding their tandem throughout the state looking for new challenges on hilly back roads. Krystek has mapped many bike rides in Wisconsin since the late 1970s, most recently designing routes for the Horribly Hilly Hundreds and the Insane Terrain Challenge.

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