Why I’ve Ridden My Bike Up the Same Mountain 385 Times

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Five measly seconds.

It’s the duration of a long fart or a short text message. There’s a reason the five-second rule applies to a dropped Cheeto—it was barely on the ground!

Alas, this tiny amount of time separates me from achieving the only athletic goal I have cared about in decades. On a crisp morning last October I slumped over the handlebars of my road bike, gasping for air and fighting back the urge to puke. I had just raced my bicycle up Flagstaff Road, one of the popular paved climbs here in Boulder. My objective was to break the magical 30-minute barrier on the climb’s Strava segment, which is called Super Flag.

My legs throbbed, my lungs burned, and I tasted blood—all signs that I had pushed my body to its physical limit. After the pain wore off, I opened the Strava app and peered through sweat at my finishing time: 30:04. I was five seconds from glory.

I wanted to both cry and laugh at the absurdity of having pushed myself to the brink and come up short by a long fart’s—or short text message—worth of time. As I caught my breath, I realized that my bewildering reaction was connected to Flagstaff Road itself. This five-mile stretch of pavement, rising 2,200 vertical feet from Boulder’s leafy neighborhoods to a collection of mailboxes surrounded by conifer trees, had come to play an outsized role in my life.

Over the past few years I have obsessively ridden Flagstaff Road, logging no fewer than 385 ascents since 2019, according to my Strava data. As of the publishing of this story, I have completed 65 ascents of it in 2024 alone—that’s about once every two-and-a-half days. I ride Flagstaff in every season, climbing it in sunshine, rain, and even snow. Some days I ride it hard, other days I go easy. On some mornings I will complete three or even four ascents before work. On a chilly evening this past October I strapped blinky lights to my handlebars and helmet and rode Flagstaff at midnight under a full moon.

To be clear: I am not bragging about my fixation with this climb. This is entirely a confession of neurotic and Sisyphean behavior that absolutely defies logic. Flagstaff isn’t even my favorite climb, nor is it the best road ascent here in Boulder. The super-steep Magnolia Drive is harder. Sugarloaf Road boasts prettier scenery. There are far fewer cars driving along Deer Trail Road or Super Jamestown than there are on Flagstaff. And the Gold Hill General Store, with its delicious homemade cookies, awaits anyone willing to ride Sunshine Canyon Road all the way to the top. But still—I ride Flagstaff Road.

There are, of course, hundreds of Flagstaff Roads across the country—popular ascents that become the focal point of obsessive personalities. Old La Honda Drive, Emigration Canyon Road, Glendora Mountain Road, Bear Mountain, Lookout Mountain, to name a few. I’ve ridden many of these ascents before, and I’ve heard tales of cyclists who ride them every day, day after day, rain or shine. A decade ago I never would have predicted that I’d someday join the ranks of the single-climb-obsessed, but here I am.

It wasn’t always this way. Back in my twenties I indulged in long and carefree rides on the many climbs dotting Colorado’s Front Range, rarely ascending the same incline more than once in the same week. In that chapter of my life, riding a bicycle fulfilled my bottomless appetite for freedom, and I faced zero consequences if a pre-work excursion went long, or if a weekend adventure lasted for six or seven hours.

And then I grew up and entered middle age. Greater professional responsibilities torpedoed those mid-week hooky rides, and marriage and parenthood made my hours-long weekend outings a thing of the past. New stresses and pressures entered my life as I joined the American middle-class: mortgage payments, tantrums, insurance premiums, backyard sprinkler systems gone haywire. My bicycle took on a different role in my life—rather than a vehicle for adventure, it became equal parts workout tool and stress-busting weapon. My rides shortened and intensified, and I focused on incinerating calories and dousing my synapses with endorphins.

Instinctively, I sought out the hardest climb that required the shortest distance to and from my office and my home. An ascent where I could punish my legs and lungs, burn off the workday tension, and be back at my desk in an hour flat. One climb fit the criteria: Flagstaff Road. I started riding it on weekdays, then weekends. After my daughter was born in 2019, my ascents became more frequent.

Convenience pushed me to Flagstaff Road, but an altogether different dynamic has kept me coming back. Over time, those repeats tattooed the roadway onto my brain. After a few hundred ascents, I memorized the gradient of every switchback, and the placement of every pothole. I could guess my ascent time to within 30 seconds based entirely on my perceived effort. Put a blindfold on me and I could ride to the summit and back without incident.

With such familiarity, my riding style changed. I could switch off the parts of my brain that focus on time, direction, and spatial awareness, and instead focus on areas of my life that required attention: the cause of an argument, solution to that financial setback, the structure of a column that wouldn’t quite write itself. Sometimes, the mixture of hypoxia and lactic acid helped me find solutions to my woes. My senses became hyper-attuned to the variations caused by seasons, weather, or time of day. I studied the different smells that wafted across different sections of the ascent: wildflowers, pine needles, damp grass, hydraulic brake fluid.

I have, at times, worried that this obsessive riding would lead to boredom and burnout, and I have hypothesized that my repeats are simply an extension of the banality of suburban life. Chop wood, carry water, pedal up a ribbon of asphalt aboard an expensive bicycle, then repeat. But there’s a different type of freedom that occurs during my Flagstaff rides. I have no clue the places my mind will go between the first pedal rotation and the last, or what grand conclusions I will come to about parenting or writing during my five-mile ascent.

I am not alone, and in recent years I have seen the same bicyclists riding Flagstaff Road, all huffing and puffing and working out their problems a few times each week. There’s Randy the physicist, Miguel the dad, and a grandpa in DayGlo who rides before the sun comes up. I recently read on Facebook that my old Yoga instructor biked up Flagstaff 126 in 2023. And every June, a group of Boulderites all ride Flagstaff Road every day for an entire week. Organized by the co-founders of the local boutique bike brand Mosaic Cycles, Flagstaff Week is a celebration of the climb and those who worship it.

I asked Aaron Barchek, one of the ride’s founders, why Flagstaff Road grabs ahold of some of us, and compels us to ride it over and over again.

“It’s the one climb that everybody knows,” he told me. “It’s the proving ground for Boulder. Everybody knows their fastest Flagstaff time.”

For now, my record will remain at 30:04. I raced up it during Flagstaff Week in early June, and again slumped over my bicycle at the top, gasping for breath. My Strava time read 30:44. I’m not getting any faster, but I’ll keep coming back.