A Ride Across America: the Road, People and Lessons Learned

by Thomas Wilson ’25

^{Above: After 4,300 miles on the road, Thomas Wilson ’25 finally made it to the Golden Gate Bridge. (Photos by Zach Thompson)}

After graduation, I wanted to take a trip before settling into whatever came next. I’d lived in the U.S. for almost four years, but had only really seen the East Coast and the cities I’d traveled to for soccer. Before moving here, I thought of America mostly in terms of its big cities – New York, Miami, Los Angeles, Las Vegas – but during college I learned more about its national parks and realized how much of the country I hadn’t experienced. My first plan was a traditional road trip by car, but the idea of crossing the country by bike felt truer to what I wanted: to move slowly, see things properly and really earn the views out West.

At first, it was just a vague idea to fly to California, cycle around some national parks, and see where it took me. That changed in the fall of my senior year during an entrepreneurship class called Intentionality, which focused on a different theme of self-improvement each week. The topic that week was stepping outside your comfort zone, and I realized the last time I’d truly been uncomfortable was when I first moved to the States.

Our guest speaker that day, Charlie Layton, had rowed a boat across the Atlantic. In passing, he mentioned that when he first moved to the States, his company gave him the “company car,” which turned out to be a bike that had already been ridden across America. His story about rowing was inspiring, but that one line about the bike stuck with me. I had no idea it was even possible, and it made me realize the trip I’d been planning felt too safe.

When I told my parents about the idea, the reaction was mixed. My dad said, “no chance,” while my mum was similarly taken aback, but slightly more open. I don’t think they believed I was serious – and, to be fair, neither did I at first.

Later I learned that Ben Towill, the owner of Basic Projects in Charleston, was the one who had ridden said bike across America. I reached out, and, when we met, his whole face lit up talking about it. That conversation stayed with me, and by December I’d decided to go for it.

That spring I started training and planning. Through a mutual friend, I met Zach Thompson, a photographer and videographer who’d just gone freelance and had dreamed of doing a similar trip since he was a kid. After a few meetups for coffee and some training rides, we decided to go together. We barely knew each other, but I figured anyone who was willing to bike across America for the hell of it was someone I’d likely get along with. I’d originally imagined a trip like this being something to be done alone, but looking back, I’m so glad I was in it together with someone else. Having someone to recount the day while cooking over our camp stoves in the evenings, sharing the views, and even the silence, made the trip all the more human.

On May 13, we set off: two bike-packing novices on loaded bikes, heading west with no real idea what was ahead. My parents joined for the first week, which made easing into the everyday flow of things much easier. They tagged along in what we joked was a Tour de France-style support wagon, while also getting some miles in the saddle themselves.

The ride was tough in all the obvious ways, but what surprised me most was the mental side of it. We averaged around 70 miles a day, often on long, empty roads with nothing to do but think. Cycling like that is slow enough that you can’t hide from your own thoughts, so there was plenty of time to consider the future.

I hadn’t yet landed a job but was hoping to secure something during my year of postgraduate work authorization in the States. The clock was ticking, so I was still submitting applications and even doing interviews from the road. Some took place behind a QT gas station, in the bedroom of an Airbnb and in a pie shop in the middle of Kansas. I like to think I’m the only person who’s ever started an interview apologizing for the dodgy signal, sunburned face and fluorescent cycling top.

Some stretches were absolutely stunning, and the miles flew by; others tested every bit of patience I had. In Nevada, the road would stretch straight for 10 miles, slightly uphill, with a steady headwind that made it feel like we were pedaling in squares. Looking up after half an hour and seeing the horizon unmoved was brutal. I played music and podcasts to pass the time, but mostly I learned how to sit with boredom and notice the small things.

A constant presence throughout the trip, oddly enough, were cows. They’d watch curiously as I rode past – and, one day, I myself got too curious and got zapped by an electric fence while trying to pet one, which taught me my lesson. A running joke with David, a cyclist who joined us for much of the trip, was that every other photo on my phone featured a cow, and he wasn’t far wrong. My favorite was in Kentucky:

One day in Utah summed it all up. I was riding alone for a week while Zach went back to Charleston, and I’d been dreading a 120-mile stretch through the desert with no towns, no gas stations and only one muddy river for water. At the final stop, I loaded nine liters onto my bike, and a couple I’d met insisted I take their water purifier, saying it might come in handy.

That day hit 103 degrees. My bottles were almost boiling, and by mile 85 I was out. When I flagged down a passing car, the driver, who turned out to be a cyclist, gave me the rest of his water. Ten miles later I was empty again, and another driver stopped to hand me ice, snacks and soda. It was enough to get me through. When I finally reached camp, I found a group of geologists setting up their tents. They had coolers full of water and food and immediately invited me to join them. Sitting in the desert that night, sharing dinner and a beer with strangers, ended up being my favorite moment of the trip. It had everything: exhaustion, beauty and kindness.

That kindness showed up everywhere. People bought our groceries, offered us places to stay, ordered us pizza or simply waved from their cars. Once, climbing out of Yosemite on a long uphill stretch, I was completely spent when a car pulled up beside me, tossed a pack of fruit snacks out the window, shouted something encouraging and sped off. It sounds small, but it meant everything at the time.

If I learned one thing, it’s that you don’t need perfect conditions to start something. I’ve always been someone who plans, waits until things line up and overthinks timing. But on this trip, things went wrong constantly: We had flat tires, broken spokes, forest fires, bad directions, and just had to keep adapting. We knew that if we kept moving west, we’d eventually reach San Francisco.

At first, I hadn’t planned to ride for charity, but the more I trained, the more it felt wrong not to. I’ve been about 80% deaf since I was 17 because of a condition called otosclerosis and have relied on hearing aids ever since. They’re expensive, and I know how lucky I’ve been to have access to them. So I partnered with the Hear the World Foundation, which provides hearing care for children in low- and middle-income countries, and we raised $2,500 along the way. On the hardest days through Kansas wheat fields that never seemed to end, or the dry heat of Utah, remembering that I was riding for something bigger than myself helped me keep going.

I started this trip wanting to see as much of America as possible before life pulled me elsewhere. I finished it realizing that what makes a place unforgettable isn’t the landscape or the miles you cover, but the people you meet when you’re vulnerable, open and moving slowly enough to notice.

Thomas Wilson ’25 grew up in the Lake District in England, and came to the College to play soccer and major in economics. He is currently a business analyst at LoanBoss in Charlotte, North Carolina.