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A few years ago, after a decades-long, 60,000-mile-plus love affair with road cycling, I started dabbling in mountain biking. I did this largely because I’d moved from New York City, where the discipline was essentially alien, to New Jersey, where the off-road riding was not only close by, but surprisingly good and abundant. I initially pictured the transition to be merely a shift in terrain. A bike is a bike, after all. But I was vastly mistaken. Like anything in the world of cycling, mountain biking comes with its own inscrutable rules and mores, its own fiercely inhabited subcultures, and its own baffling array of clothing and equipment choices. Did I need a trail bike? A cross-country bike? A “downcountry” bike? How much travel did I need in my suspension? Did I need 27.5-inch wheels, or the 29-inch variety? Never had I seen 1.5 inches loom so large in people’s worldview.

But soon enough I was out on my local trails. Like beginner drivers, my motions were twitchy and hesitant, my focus almost entirely on what was directly in front of me—every fearsome root and rock flooding my brain with data. In road cycling, the asphalt you’re riding on, barring a pothole or two, is an afterthought. But in mountain biking the surface was a moving puzzle, requiring careful attention, planning, and decision-making.

I plodded along, my improvement hindered by the inconvenient fact that, for me, mountain biking requires driving to a trailhead versus riding straight out of my garage. So I usually default to road riding, keeping my mountain-biking mediocrity safely intact.

Thus was the state of affairs when, one weekend last summer, I was invited to ride in Vermont with a group of friends. There would be some gravel riding—more equipment choices, more rules, more subcultures—and some mountain biking, including a visit to . I had been dimly aware of the movement by ski resorts to try and generate summer dollars by ferrying cyclists on lifts up to their snowless summits, but I’d never stepped foot in such a place. Which was quite obvious to me when I arrived at the so-called Beast of the East wearing shorts, a T-shirt, and a traditional bike helmet, and found myself amid what looked like a casting call for Mad Max Beyond Thunderdome; it was packed with dusty men and women, with thousand-yard stares, wearing body armor, neck braces, and full-face helmets. A sign, no doubt crafted at the behest of a lawyer somewhere, warned: “Injuries are a common and expected part of mountain biking.”

A friend glanced at my bike and advised me to lower the seatpost: “You’re not going to be pedaling much.” That’s when I realized I’d never bothered to set up the dropper post on my Canyon Neuron. Coming from road riding, where a precise saddle height is sacred and Never to Be Changed, I figured it’d be superfluous. (And, full confession, I couldn’t figure out the install instructions that synced up the little switch on the handlebars to the seatpost.) I hastened to the repair room, where the park’s mechanics quite graciously set up my post in a matter of minutes, making no comment about this forehead-slapping moment in noob history.

We hoisted our bikes onto the lift, rode to the top of Snowshed, home to the beginner terrain, took in the verdant, panoramic view, and then headed down Easy Street, one of the park’s few green runs (bike parks, I learned, retain the green-blue-black rating system utilized by ski areas everywhere). I rode it, tentatively and with excessive amounts of braking, entering the precisely sculpted banked berms low and exiting high, exactly counter to how it should be done. For my efforts I was rewarded with a more technical blue trail, known as Step It Up. According to Strava, I was among the slowest riders to ever descend that route—I ranked 5,077 out of 5,459—but it still felt like I was flying. And then, a minute or so into the ride, I encountered a sloped earthen structure looking like one of the . This was a “tabletop.” It is meant to be jumped. But it was also, as they say, rollable, meaning it could simply be ridden over. Which I kept doing: barreling toward the upward slope before suddenly freaking out and jamming on the brakes, trying to maintain control as my body pitched forward.

That afternoon was a revelation. Normally, in my cycling life, I’ve suffered on the climb and been rewarded on the descent. Killington flipped that idea on its head. Here I suffered on the descents—my heart was in my throat, my hands, back, and knees were on fire, I crashed more than once—and was rewarded with a tranquil, breezy lift ride to the top. (And whatever you may think about the lack of pedaling, at least has found that the majority of a downhill ride results in a heart rate in “a zone at or above an intensity level associated with improvements in health-related fitness.”)

But I was left with the nagging feeling that I’d left something on the table—or the tabletop, more precisely. I wanted to know what it would feel like to leave the ground on my bike. I wanted to catch air.