How I learned to ride a bike for the first time, at age 27

I never actually learned to ride a bike as a kid. I spent many hours on a tricycle when I was a toddler; the trike just became less appropriate when I physically outgrew it. My friends, on the other hand, all received sparkling new Schwinns. They’d spend their summers cruising around New York suburbs’ sidewalks, weaving in and out of traffic as I watched from afar.

Simply put, it sucked. Hard. I tried and failed numerous times to balance on a beat-up girl’s bike at my grandparent’s house, but I always fell. For two decades, I attempted to ride on friends’ and family members’ bikes, but only ever moved a couple of feet before I’d nervously tip over onto the sidewalk and panic. After attempting and failing to balance on a friend’s bike in Prospect Park in 2009, I all but gave up on biking for good.

The idea of getting back onto a bike came to me five years later, when I lost my editing job in the summer of 2014. All my newfound free time as an unemployed adult came with a new determination to check off some major to-do’s in my life: applying to grad school, finishing The Wire, and, of course, learning how to ride a bike.

The first two proved to be particularly soul-crushing, while the latter seemed rather silly at the age of 27. I could do my own taxes and had taught myself guitar, but I still couldn’t get on a bike.

A simple Google search brought Bike New York’s adult bike-riding classes to my attention. The NYC-based not-for-profit teaches adults of any age how to ride a bike in all five boroughs for free (pending a $50 charge on a credit card if you no-show, as added incentive) with volunteers around to help people who’ve never been on a bike before or have always feared being on one.

I signed up for a mid-afternoon class in Staten Island, with the thought that should I attempt to ride a bike this time — which I would most certainly fail to do — I would at least do so knowing that no one I cared about would watch me. So on August 10, my fiancee and I took a bus over the Verrazano Bridge, got off at the first stop, walked through the nearby military base, and made our way to the beautiful Fort Wadsworth Park adjacent to the bridge.

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In the rear of the park sat a coned-off lot on a slight incline, with dozens of bikes and helmets strewn across the lawn. Men and women of all ages, from 18 to 68, gathered around as the instructor (whose name escapes me) taught everyone the basics of a bike, which I’ve heard a million times and didn’t really pay much attention to. But when she told us that we were all going to learn how to ride without pedals, I was confused. After all, isn’t the whole point of riding a bike pedaling the bike?

Before I could compute the logistics of a pedal-less bike, we were all given a bike that fit our height, a neon-colored helmet (the ones they give out for free at street fairs), and instructed to balance the bike as it rolled down the incline. At first, I moved every few feet until I fell. It seemed like a futile exercise, one that I repeated for the last 20 years with no hint of progress.

After 20 minutes, however, I was able to move 10 feet without tripping myself out of nervousness. Soon after that, I could move 20 feet, then 30, then down the length of the parking lot without falling. Sure, braking wasn’t a thing I was used to yet, as I crashed into a few road cones here and there on my way down the hill, but I was actually balancing a bike for the first time in my life without falling.

When the instructor thought someone was making enough progress with their gliding, she would send them over to volunteers on the side of the lot to add pedals to their bike. Now that I got the hang of gliding, I gained the use of pedals and tried to actually ride a bike for the first time. Sure enough, after a few more glides around the lot, I finally started pedalling…and immediately turfed out.

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All-told, it took me 45 minutes to learn how to ride a bike after 20+ years of being afraid to do so. I wasn’t just riding every dozen or so feet and stopping short. I was actually pedalling around the parking lot in laps (laps!), braking a bit hard, but getting the hang of the one thing I was deathly and irrationally afraid of. Some students gave up before they had the chance, but most of us that day had finally learned how to get on two wheels and ride as far as the tiny lot would let us.

I felt free. And I wanted more. As soon as I got home, I scoured Craigslist for a cheap bike, eventually settling on a kitschy ‘80s mountain bike I scored for $200 in Park Slope. After buying a helmet, some lights, and a few accessories, I finally felt comfortable enough to bike around New York for the first time in my life.

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Since then, I’ve biked over 1,500 miles around New York and New Jersey. I got used to inclines by biking up and around Prospect Park, eventually conquering the monster of a hill at the tail end of the park’s circuit after over a dozen failed attempts. Soon, I was biking over bridges, along the east and west side trails, and accidentally maneuvering into rush hour traffic. When I finally found employment again, I started biking to and from work, taking a bit more time than the train commute but with significantly more breathing room. I replaced my long walks with longer rides, ventured out to places in Brooklyn I wasn’t too familiar with, and discovered beautiful parks that I now visit every week.

For the years that I didn’t know how to ride, I always thought that the prospect of learning late in life was embarrassing and shameful. I felt it would forever be a strange anecdote that would come up at parties or get passed off as a joke at family gatherings. Once I finally got on a bike, however, I haven’t been off one since. Except for the time I got hit by a cab.

Follow Scott’s freewheeling tendencies at: @ScottFromNY

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