The wheelie has been vexing riders since the late 1800s, when the penny-farthing—with its giant front wheel, tiny rear wheel, and saddle four feet off the ground—gave way to the more user-friendly “safety bicycle,” with wheels of equal size.
The father of the wheelie was a telegraph messenger named Daniel J. Canary, a “fancy riding” champion who figured out how to coax the penny-farthing’s rear wheel off the ground. In August 1890, he used a safety bicycle to pull off “the feat, then regarded as impossible, of riding on his rear wheel, with the front wheel elevated.”
That’s how the Chicago Tribune described the wheelie in 1896. The article, titled “Wizards of the Wheel,” chronicled the origins of “trick riding” and noted why the discipline had but a few bold pioneers: “The union of strength and agility with perseverance and self-confidence is not common enough among men.” (It said nothing of women.)
“Like the art of the contortionist, trick riding requires an extraordinary suppleness of body and limb,” the author wrote, adding something that rings as true today as it did 125 years ago: “United with this must be the patience and perseverance for long and unremitting practice.”
Extraordinary suppleness is overrated. Those last four words mark the difference—then and now—between Wizards of the Wheel and wannabes.
It turns out that long and unremitting practice hurts. After day one, I feel like I’ve been flagellated with bars of soap in tube socks. I quickly call upon some experts.
Lindsey Richter, founder of the Ladies AllRide women’s mountain-bike camps, says the wheelie is primarily about torque—getting the back wheel to accelerate with enough power that the front wheel rises. To make this happen on a motorcycle, you either rev the engine and dump the clutch, or simply rip open the throttle. On a bike, it’s a seated, slow-speed procedure initiated by a powerful pedal punch. Your arms don’t lift the front wheel, she says, so much as they “encourage it.”
Braydon Bringhurst, a Canyon Bikes ambassador who can land a backflip in a wheelie, instructs me to drop my saddle two inches, lowering my center of gravity, and practice by placing two objects—cones, rocks, gloves, whatever—a few feet apart as a target distance. Once I can wheelie that eight out of ten times, he says, I should move them farther apart.
When I watch teenage boys manual the waves of dirt on a BMX track, a little voice whispers, Maybe in your next life.
From my buddy Lance Trappe, who rode for Cirque du Soleil, two shows a day, 478 shows a year, for 14 years: Move your knees from side to side for balance. Also, practice on a smooth surface and an uphill slope. But the secret sauce, he says, is the rear brake, which brings the front wheel down to guard against loop-outs.
So my mission for the next few hundred wheelies is to train my right index finger.
Not to brag, but I have an extraordinarily supple index finger. It can strum a guitar, pull a trigger, deadhead daisies, maneuver a paintbrush, give directions, and pick anchovies off pizza. It knows damn well how to feather a brake.
But something short-circuits when my front wheel takes flight. All I ask of my digit is a crummy millimeter or two of precise modulation. Under pressure to save me from looping out, it chokes. I spend hundreds of wheelies yelling at my finger like a drill sergeant. It’s as useless as a football bat.
Meanwhile, the manual seems even more hopeless. After my crash, I buy knee pads and practice on a baseball field. The grass scrubs my speed, which makes my handlebars wobble. I land on a turned front wheel and am ejected into left field, where I pick dead grass out of my teeth.
At the next session, Kenny arrives with two gifts: a full-face helmet, donated by a buddy who works at Fly Racing, and the suggestion to look into a manual machine.
A manual machine is basically a float-zone simulator, designed to help you locate the balance point while a static contraption holds your rear wheel safely in place. Sender Ramps, a company in Seattle, ships me its Core Skills Trainer manual machine, which Austin and I assemble with a power drill and minimal bickering.
In the safety of the garage (my husband vetoes the living room), I find the balance point after six tries on the manual machine. The sensation reminds me, unexpectedly, of my days as a competitive water-skier. My muscles begin to memorize the dance of opposing forces—pulling on the handlebars, pushing against the pedals—and the hip action that occurs in between, a quick and thrusty motion that mortifies my husband when I mime it in public.
The manual machine bewitches my son, who sees it not as a training tool but as a giant toy. Austin suddenly opts in to the wheelie quest. Like most kids, his athleticism far exceeds his patience, and any skill that doesn’t come easily is soon crabbily abandoned. But as we try and fail, heckle and laugh, I notice a new quality sprouting within him: perseverance.
When the pandemic hits in March, wheelies become therapy. The bike park shuts down, so Austin and I practice in the street, where we’re cheered on by neighbors. Our ritual gets my kid out of the house and me out of my anxious head.
My first big breakthrough comes with Wheelie No. 681. I enter the sweet spot—and stay there, for 12 pedal strokes. My gleeful cackle is a noise I haven’t heard in a while. The stoke rubs off on Austin, who also has a quantum leap in the float zone.
When I head to a mountain cabin for a writing retreat a week and a half into the challenge, I bring my bike and practice alone in the snow. On the edge of a frozen lake, with a light post as my target, I keep Wheelie No. 1,086 in the float zone for what feels like an eternity. After, I pace off the distance, counting each stride: 17 steps, around 34 feet.