The guy cruising along next to me says “Well, this isn’t so bad, is it?”

“Not really,” I respond. Looking down at the computer, we’re about six miles into the Insane Terrain Challenge. “I bet within the next five miles we’ll be climbing though.”

Ha! A half-mile down the road we take a left turn and it began – relentless climbing, false flats that played games with my mind, and a whole lot of solo riding.


The alarm clock didn’t go off at 2:30 Saturday morning as I had set it for. At 3:45 I opened my eyes, looked over at the clock and let out a couple of profanities. I had wanted to get on the road by 3:30 at the very latest, considering that the drive to Blue Mounds was estimated at about two hours and fifteen minutes. I showered quickly, got the bike in the back of the Element, and assembled my riding gear within twenty-five minutes. I was on the road at 4:19. Rain was coming down.

Driving on I90 through Rockford made me wonder what kind of ride I’d get in. Twenty miles? Ten? The full seventy-seven? None? I had put faith in the weather map I saw Friday afternoon that showed no rain for the Madison area. But at 5AM, the Rockford area was practically underwater. Still, I saw some vehicles with bikes inside, traipsing over the dark, wet roadway.

The further I made it north, the less rain there was. (Actually, around the state line the rain disappeared.) Around 5:30 I started calling Zach and Dave (who had driven up to Madison from Chicago Friday night to let them know where I was – and also to ask if they could pick up my registration packet, as I wasn’t confident in making it to the start before the stated 6:30 ride start. At 5:45 I got a hold of Dave – from then on we played phone tag, figuring out how to get to registration at Blue Mounds State Park.

Finally at 6:40 we made it to registration. After we got our packets, Dave’s father and his buddies started showing up. I changed into the Half Acre jersey, gloves, and an old pair of Specialized bibs (even though the skies were clear, I didn’t want to risk getting the Half Acre bibs dirty and greasy from wet roads -- of course, I did not feel one drop of rain during the ride). Zach and I both changed tires, my rear wheel from the trainer tire, and Zach’s front from a sliced tire. We ended up descending the road from the park around 7:25 or so. Only two riders started after us.

I felt a little squirrely starting out; I haven’t raced yet this season, and we were in a paceline from the get-go. The legs felt fine, as they should have – afterwards, I found that the first few sections were actually downhill.

Around mile seven the hills started. Bam, the “elastic broke.” Of course, the elastic was holding me onto the group. I settled into a rhythm though, kind of like when I rode centuries relatively consistently, and just kept moving. Some miles were spent riding along John from Rockford. Neither of us had the miles in our legs that we should have, and it showed.

At the first water stop, Zach said that I was only a few minutes behind the group. I’m sure he was being kind. My strategy of motoring along at a comfortable pace seemed to be working though, as I was feeling pretty good.

John and I rode a good chunk of the way to the fully-stocked rest stop together. Towards the last part of the section, he had moved ahead of me by about a minute. I thought I saw him up in the distance, and reeled him in, except that it wasn’t John – it was a guy struggling mightily on a flat-bar road bike. Heck, at least I passed someone. Heading into the town of Mineral Point, I took two lefts. The first brought me towards town, and the second took my up a climb (my guess is that it was a 10% or more grade). Pulling hard enough on the bars to pop a few wheelies, I finally saw the rest stop at the top of the climb.

I found out that Zach and one of the Rockford guys blew right through the rest stop – Zach didn’t even notice that they had passed it. The rest of the Rockford group and Dave were there. I drank a good amount of Gatorade, had a couple of granola bars, and talked with a few people for probably too long. Dave and the Rockford group left about five minutes before John and I did, which was fine with me. Additionally, the two riders that started behind us left before we did. I was there to get miles in my legs, and if that meant riding a slower pace and recovering a bit at the stops, so be it.

John and I rode out of town together, and cruised down Wisconsin route 39 for a bit before the route took us left (east) on County DD. From there, we would continue east for about twenty miles until we entered the town of Blanchardville, where the next rest stop was.

On DD, the climbs started, and I settled back into my pace, maybe a quarter-mile per hour slower than John. The landscape reminded me somewhat of a greener, hillier Texas Hill Country. This farm-field section exposed us to the sun and the humidity though, as there wasn’t many trees to provide a wind break.

About five miles into the section, a sag wagon pulled alongside me.

“Do you know if you’re the last one?”
“How do you know that?”
“We were the last to leave the rest stop, and I haven’t passed anyone.”

Jeez, don’t rub it in dude, I thought while smiling. Heck, we were pretty much the last ones to start! The thought went through my head that maybe I really didn’t care if I was the last ride on the course. Maybe that was a lie.

A couple of miles later I see John and the two late-starting riders about a half-mile in front of me. I didn’t crank it up a full notch, but isn’t it every cyclist’s nature to try to reel in any rider in front of him? A half-notch it was then. I slowly started gaining on them, little by little I was going to catch up to them, talk for a while, and then cruise on ahead.

I was wrong.

At mile 46, about halfway up a hill that was between a real climb and a roller, both of my quads started the dreaded cramping cycle. For the second time that day, I let out some profanities. I’ve experienced leg cramps enough times before to know that I was in for a lot longer ride than I had expected. I immediately shifted to the 39:25 and spun for the next half-mile or so. Strange – the legs don’t feel all that bad, I thought. Another hill, a bit steeper than the one before, loomed in front of me.

At the base, the legs just went. The calves started to tighten a bit, but the quads were the source of my pain. An image of a television news map showing the affected areas of an earthquake stuck in my brain – the epicenter was the inside quadriceps of each leg, with the flashing red circles emanating from there.

I looked up and saw the same Subaru sag wagon as before. I waved him over, and I sagged out of a ride for the second time in my life. Forty-seven miles and almost 4,700 feet of climbing had beaten me.


Zach didn’t look too much worse for the wear at the finish. Dave on the other hand did – “never again” might not have been his exact words, but I think they are close. I bet he’ll be back next year.

I will too. This route will not beat me two years in a row.


-Jason Henry