From a flat Belgian side street, the road becomes a wall. The hill is only 600 meters long (less than half a mile), but from its base it looks insurmountable. I’ve been in the saddle for more than six hours already. I crane my neck to see the summit, and tremble.

“What the fuck is that?” asks Andrea.

“Koppenberg,” I answer quickly, trying to limit the breath I use.

“Oh, Jesus,” he says. Somebody laughs.

I’m riding one of the world’s hardest sportives, the We Ride Flanders, a 229km odyssey through the cobbled Flemish Ardennes in Belgium. The route follows the same roads that professional riders will tackle the next day in the Ronde van Vlaanderen, or the Tour of Flanders. By my side are three of my best friends: Andrea Sala from Italy, Mateus Pimenta from Brazil, and Michel Radermecker from Belgium. After riding 160 kilometers, a mix of flat terrain and some nasty hills, we suddenly face the hardest climb of the day.

Tour of Flanders 2018pinterest icon
The writer, in black, leads a small group.
Courtesy Sportograf

It’s just rained gently, and the sharp, irregularly shaped cobblestones are covered in a greasy film. The road looks like a war trench dug into the side of a hill. Dozens of people are walking up the edges. Some riders have mud-splattered calves as if they just ran a cross-country race. A few have mud on their faces.

I shift to a low gear from the start, but my muscles burn right away. The freshness and the agility that I felt on the day’s first climbs are a washed-out memory.

I shift once more, but the lever mushes against the end of its throw. I’ve reached the lowest cog of my cassette, my 32. I am only 50 or 60 meters in, and I am out of string in my bow already.

My journey to this muddy hill in the Ardennes began five months earlier in a gloomy pub in West London. It was November, and Andrea, Mateus, Michel, and I had gone out for a couple of beers. Several drinks in, we had a brilliant idea: We each picked two big cycling events that would take place in 2018, wrote them on a piece of paper, and put the slips into a hat. We asked a stranger—a woman who was drunker than we were—to pick one. When we unfolded the chosen slip, we knew we had a fight ahead.

For more than 100 years, the Ronde van Vlaanderen has captured the imagination of pros and fans alike. Together with Milan-San Remo, Paris-Roubaix, Liège-Bastogne-Liège, and Il Lombardia, it’s one of the five Monuments in cycling, among the oldest one-day races on the UCI calendar. Flanders, Roubaix, and LBL each hold sportives for amateurs the day before the pro race (Lombardia has a fondo the day after, and San Remo offers one in June). For the past 27 years, the We Ride Flanders sportive has allowed any cyclist to experience the sensation of riding the same roads as the pros. Each year something like 16,000 riders take part in one of four routes: 74km, 139km, 174km, and 229km.

Tour of Flanders 2018pinterest icon
Courtesy Sportograf

Of course, my group went for the big one.

We thought we were prepared. We’d double-taped our handlebars and installed wider tires. We’d watched old editions of the race on YouTube. For months, while playing back race videos, I had focused almost obsessively on the Koppenberg, the steepest hill on the route, and often the one in the worst condition.

The first time the hill was featured, in 1976, even Eddy Merckx (who won Flanders in 1969 and 1975) had to dismount his bike and push. In 1985—still remembered as the toughest edition of the race, thanks to a storm that blew in torrential rain and winter temperatures—only two of the 173 riders were able to pedal to the top (and only 24 got to the finish line).

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Part of me knew that I should be humble and should fear this iconic climb. But a combination of hubris, the flattening visual effect of camera angles, and my confidence in modern-day equipment made me think it didn’t look that bad. I considered the numbers: At 600 meters long, the Koppenberg has an average gradient of 11.6 percent, with a max of 22 percent. Having climbed the famed Monte Zoncolan in Italy (10km at a 12 percent average grade, with a 22 percent max), I thought the climb would be doable if approached with the right gear and at the right pace.

The Koppenberg had different plans.

I am on the hardest part of the climb. The road seems to get narrower. I start to zigzag left and right to slalom around riders, overtaking a few. My legs ask other parts of my body for help in pushing. My shoulders respond and start to move left and right, attempting to put more weight on the pedals. My computer says my heart rate is almost at 180 bpm. But I am determined to stay on my bike.

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Courtesy Sportograf

The repetitive impact of the sharp cobbles makes my muscles feel like they are detaching from my bones. The person in front of me cuts left. I have no other choice—I swerve left as well. I was already at my limit, crawling, and I don’t have enough strength to sprint around him. Suddenly, both wheels are in the mud. To keep from tipping over, I put my right foot down.

It’s over.

I unclip my other shoe and get off. I feel drained, disappointed, and embarrassed. Voices whisper in my head as I imagine friends asking about the ride: “How was the Koppenberg?” “What? You didn’t make it?” “Did you put your foot down?” “He went all the way out to Belgium and walked up the Koppenberg!” I try to get back on my bike, but the road is too crowded and slippery. Within two pedal strokes, I am off again.

Walking uphill is probably trickier than riding. The sound of carbon soles scrabbling against the slick cobbles mocks us, and a dark cloud of dismay descends over me. I feel stupid and defeated.

At the top, we pull over and regroup. “Who actually made it?” asks Michel. What he really means: Who rode it the whole way? I shake my head.

“I had to walk for a bit, and then got back on the bike after,” says Andrea.

The only breath Mateus musters is invested in a loud curse.

We all laugh.

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Courtesy Sportograf

Since the beginning of the day, a silly Brazilian samba song has been stuck in our heads (“E Samba” by Junior Jack). As we roll off, I start to sing it out loud, though I don’t know the lyrics, so my version sounds like gibberish. We laugh again. The jingle gives us some spirit with which to fight the Flemish roads.

A gray mantle of mist decorates the green hills of Oudenaarde. The air starts to get crisp—it is almost 4 p.m. in late March—and it is getting dark. The last 32km turns into a silent procession.

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We hit the Oude Kwaremont (2.2km of rolling, bone-rattling cobblestones), then the road turns to smoother asphalt. An event marshal appears, waving for us to slow down. I look to my right and see the other cobbled climb we’ve been anticipating: the Paterberg.

The Paterberg is a little less steep than the Koppenberg and the surface is in better condition. Once more, people are walking. And again, I find myself struggling up the cobbles. The voices in my head begin whispering again.

As I grind up the steepest section, a guy in front of me starts to lose his balance. He manages to stay upright but swerves toward me. I forget about being polite and yell, “Your left!” Remarkably, he actually swerves left again, squeezing me into a narrow stretch of road between him and the mud off to the side. I suck it all in, yell again—and squeeze through.

I make it to the top on my bike. It feels like redemption.

Tour of Flanders 2018pinterest icon
Courtesy Sportograf

Before I signed up for the sportive, a friend had suggested riding one of the shorter options instead, because the first 100km of long course was, as he described it, “flat and not interesting.” Maybe without all those kilometers in my legs already, I would have been able to ride the Koppenberg. But after battling all 229km of the long course, I think the real meaning of Flanders is to ride those cobbles with the legs smashed.

Some pros, I later learn, will also walk it the next day. I’d rather walk the Koppenberg on a 229km day than ride it on an easier route. To walk is to meet your cycling limit. There’s pride in pushing to that point.

We cross the finish with nine hours in the saddle. After a bus ride back to the town where we’re staying, a short ride through the dark to find our Airbnb, and long-awaited showers, it’s 10 p.m. by the time we finally sit down and sift through the emotions of the day. But with eight pizzas and 20 beers in front of us, it doesn’t take long to start looking ahead.

“So,” Michel says. “Next year Roubaix?”