“Stand in the middle and don’t move,” Cole said.
Cole Freeman is a stocky blond stunt rider with rosy cheeks from St. Louis. Despite a recent streak of not being able to follow instructions, I felt like I should make a concerted effort to follow this one. Cole and his hype man were about to enter the Wall of Death, and in a moment, so was I.
The Wall of Death is a silo-shaped old carnival attraction that dates back to the 1900s. Two motorcycles ride along the vertical wall and perform stunts, held in place only by friction, the science of which I found dubious. Cole was smiley and fearless, and had recently been crowned the new Evel Knievel, after an official blessing from the family. Me? I was not smiley. I was terrified.
So I stood as still as possible in the eye of the tornado. They whirred around like bees, crisscrossing, high-fiving, at one point taking my hat. These guys were relaxed and having a blast, though, and once that energy rubbed off, I stopped sweating and a grin crept up my face. I still wasn’t sure about the science of it all, but I trusted Cole. It felt good.
We were in the middle of Milwaukee for the Harley-Davidson 115th Anniversary celebration, but my fear-conquering journey started a few weeks before at the Harley-Davidson of Glendale, where I was enrolled in the Harley-Davidson Riding Academy New Rider Course, a jam-packed weekend of both classroom and course instruction. I showed up to the classroom at 6:30 P.M. on a Friday night ready to learn. (Full disclosure: I had not been in a classroom setting since I dropped out of high school in the 11th grade.) To my right was a father and son, who had just graduated from high school and enrolled in the Army. To my left was a friendly woman from New York City who owned a natural-skin-care company. The rest of the class was a surprisingly diverse group: a few Porsche-driving midlife-crisis Republican types; an early-30s overachiever who was gunning for the title of teacher’s pet; a WASP-y blond guy from Boston who had ridden motorcycles in the Dominican Republic; and a soft-spoken black guy who drank a lot of soda, presumably to calm his nerves. The classroom portion was simple. Succeeding meant paying attention and using common sense. It was the riding portion, which started at the ungodly hour of 5 a.m., that had me nervous.
In a way, the classroom brought me back to high school in Conyers, Georgia. The popular kids were all hunters, the stereotypical kind who wore Bass Pro Shops mesh hats and cowboy boots, and had gun racks fastened to the back windshield of their muddy F-150s. They were loud and proud about being conservative and myopic; the kind of grown men who would go on to post Constitution memes on Facebook. Nothing seemed less interesting to me and I went the other way completely, turning up my nose in disgust not just to their obviously ridiculous worldview but to every aspect of their culture—including motorsports, which terrified me. So I dropped out of school and putzed around Atlanta for a few years, before finally relocating to New York City, where I started my own business, did drugs, and surrounded myself with like-minded liberal thinkers.
By the time I arrived at the vacant parking lot in Glendale the next morning, I was amped up on cold brew and adrenaline. I was told to grab a pair of gloves and a helmet, and all of it was starting to feel very real. The instructors were friendly enough but not super chatty as they walked us through all the basics.
Then it was time to actually ride a bike.
The thing that people don’t tell you about motorcycling is how physical it is. The bike is heavy and hot, and keeping it upright can be strenuous. You have to keep your quads and abs engaged, which is a difficult feat, especially when you have no idea what you are doing. I fudged and fumbled my way through most it. I didn’t feel adequately prepared, but I chalked that up to nerves and lack of sleep.
The test itself was focused on basics and graded by our two instructors. For the first few exercises I felt pretty good, but things went downhill fast. I bombed the sharp turns and embarrassed myself when I tried to stop quickly. The physicality of the bike played a big part, and maneuvering this hulking machine through tight turns proved more than I could handle. My thighs were sweating, and my foot kept having to go down so that the bike didn’t. It was ugly.
Once we finished, we all stood around in the midday sun, helmets under our arms, waiting for the results. It felt like the Maury Povich show with less life-altering consequences. The more animated instructor called me over, told me how much he enjoyed having me in class, and made some motorcycle-related small talk before telling me that I had failed.
Almost everyone passed. In fact, it was just me and a Porsche-driving 50-year-old dressed (prematurely) in full Harley gear who didn’t make the cut. But I had still faced my fear, and a failing grade on a test didn’t change that. I was almost proud. And definitely relieved.
This summer Harley-Davidson announced that, because of the Trump administration’s ongoing trade war, it would begin manufacturing its bikes outside of the United States for the first time, specifically in Europe. President Trump went on to publicly denounce Harley, causing a fissure in its loyal customer base, many of them Trump supporters. Some see it as a purely business move, an effort to keep prices as low as possible to attract younger customers. Others see it as treason and plan to boycott the brand. This all happened a few weeks before I was set to fly to Milwaukee for the Harley-Davidson 115th Anniversary celebration, where I found myself in the middle of the Wall of Death. It was a perfect time for a card-carrying member of the coastal elite to spend Labor Day weekend trying to conquer his fear of motorcycles while fully immersed in Harley culture for three days.
Milwaukee was beautiful, green, and felt like fall. The whole town was overrun with visiting motorcyclists. The first stop was the Harley museum, where I was given a guided tour of the facility. It was all very shiny, motorcycles and ephemera from every era on display. Fun to look at but a little clinical. We had lunch at the museum, where I struggled to order something not fried or beer-battered; the monthly special was a burger patty stuffed between a glazed doughnut bun and topped with bacon and maple syrup. I settled for an iceberg lettuce–and-tomato salad with a side of water.
Sailor Jerry Spiced Rum had generously offered me a free tattoo from Oliver Peck, Harley enthusiast, legendary tattoo artist, and judge on the Dave Navarro–hosted television show Ink Masters. I chose a snake from the Sailor Jerry flash sheet, he drew it by hand on my left forearm and got to work while a cover band played Rolling Stones songs next to us.
Oliver was upbeat and chatty. He lives in Dallas, where he co-owns Elm Street Tattoo but spends a lot of time in N.Y.C. shooting the show. We talked about sobriety, veganism, divorce, punk rock, skateboarding—all kinds of stuff. “Growing up in a punk-rock skateboarding scene, I dreamed of the days when I would be old enough to get tattoos and ride a motorcycle,” he said. I was surprised at how much we had in common. “I collect a lot of stuff,” he said. “Dice, rubber ducks, Schwinn bicycles, and Harley-Davidson motorcycles.” He said he keeps about 40 Harleys in his giant warehouse, where he also lives. His dad, unbeknownst to his mom, introduced him to motorcycles at a young age, and he fell in love. He frequently travels across the country just because he loves to be on his bike, with no distractions, his mind free and able to wander.
“The freedom of riding a motorcycle is something I never get tired of,” he said.
Running late, I rushed over to the big anniversary parade where Cole, the daredevil, was waiting on me. He told me to get on the bike for a wheelie. I was skittish, but the combination of Cole’s confidence and my successful participation in the Wall of Death calmed my nerves. I mounted the red, white, and blue bike and positioned myself as instructed: my feet on the pegs, my hands gripping the gas tank, my face relaxed, my stomach in knots, my brow soaked with sweat. Cole checked with me and then started riding, his body perched over mine in an incredibly awkward position.
We picked up speed, and the front of the bike levitated; I was floating, and I couldn’t contain my excitement, my grin was monumental, I was giggling like a child. We looped back for one more wheelie, this one lasted longer, going in circles in this parking lot, a crowd had formed, cheering us on and taking photos. Cole lowered the bike in one smooth motion, we hopped off, and he congratulated me. I took a gulp of water, and we ran over to the start of the parade.
There was no time to reflect on what I had to just done. Cole wrangled a rider near the front of the pack who let me jump on the back of his maroon cruiser. He introduced himself as Brock and he was blasting Tom Petty, which immediately made me feel comfortable.
The parade was a low-speed group ride through Milwaukee, with local residents waving, honking, and showing support the entire route. Of course, the older white folks were out in full force, but so were Muslim families, black families, Asian couples. In fact, the onlookers seemed to span a wide range of ages, ethnic backgrounds, and creeds. It seemed like Harley was much more than an expensive hunk of metal or mode of transportation; it something they could all rally around as a community. There were no apparent signs of the Trump lead boycott, but this was Harley’s hometown, where the company’s long-running success was a point of pride. If Trump’s public bad-mouthing was creating frisson in the Harley community, it wasn’t evident to an outsider like me.
We veered off and stopped in a parking lot. Brock took his helmet off to reveal model-good looks. He was a 22-year-old midwestern college hunk who had a won a summer internship at Harley. He has a radio show at MSU where he is studying broadcasting. He had only been riding a bike for a few months and was, to my mind, no way a typical Harley enthusiast. At that point I couldn’t tell if there even was such a thing.
Between sips of water, he broke it down. “I figured I would enjoy motorcycling, but I didn’t expect I’d enjoy it as much as I have,” he said. “It’s like when you’re riding a geared bike, and you start going downhill, so you stop pedaling and just cruise. It’s that feeling, only all the time.” I could learn something from Brock.
I made my way back over to the Harley museum to watch Cole and Co. at their stunt show. They did burnouts and wheelies, the crowd cheered, took photos, and drank Miller Lite in the afternoon heat. A ZZ Top cover band played in the distance. Everything smelled like burnt rubber and fried food.
I was exhausted. Even being a passenger on a motorcycle was physically taxing. The adrenaline from my midday wheelies had worn off, so I headed back to the hotel, where it donned on me that my experience with motorcycling had pitted me against the things I physically fear: speed, danger, and loss of control. I had thought that Harley enthusiasts would be similar to the hunters I loathed in high school, but I was wrong.
I needed to explore more to gain a deeper understanding of myself and others. Conquering old habits, preconceived notions, and fears. Instead of trying to enjoy something different, I avoided it and acted like it was beneath me. That had to stop. Ever since I was 12, I had been sprinting away from anything I associated with my Southern background. The fear of the machine and its powers were dwarfed by my fear of being seen as a redneck, a non-intellectual, a Republican. The people I met in Milwaukee had found their tribe, just like I did with punk rock and skateboarding all those years ago. They liked being on a motorcycle, and it created an immediate intimacy with those who shared that same passion. The bike was just a tool, a vessel that provided freedom, a simple way to bring excitement to their lives. Even though it has been politicized, the autonomy of riding and the peace of mind that it provides couldn’t be eclipsed. It was equivalent to learning the chords of a Black Flag song or landing a kickflip for the first time. Things just grab us, and all we can do is hang on with a big smile on our face. We all just want to feel free.