It was already sunny when I pulled into Foothill College, which felt deeply suspicious for 7 a.m. I expect mornings—especially Northern California mornings—to involve some low-hanging fog or at least a half-hearted cloud cover to suggest that the day is still considering its options. But no. The sky was scrubbed clean, sharp blue overhead, with the sun beaming down like a motivational speaker who’s had too much coffee.
The parking lot was already alive with cyclists in various stages of nervous preparation. Tires were being pumped, straps tightened, helmets adjusted with the kind of seriousness typically reserved for lunar launches. Small handlebar computers blinked eagerly, ready to document how much pain their owners were about to endure. I did my best to blend in, which is harder when you’re straddling a gravel e-bike at an event called The Sequoia.
An e-bike in this setting is a bit like showing up at a CrossFit competition with a Rascal scooter. Technically allowed, but quietly judged. I wasn’t here to impress anyone. I was here to basically finish. Upright, if possible.
The Sequoia had politely labeled this option the “Fun Ride.” Thirty-eight miles. Manageable. The kind of distance that sounds completely reasonable from the safety of your living room. What they failed to advertise with equal enthusiasm was the 2,600 feet of climbing folded into those miles. A minor omission, like buying a used car and only finding out later that the brakes are optional.
Chicago prepared me for many things: hot dogs, wind, and the art of pretending Lake Michigan was a beach. It did not prepare me for climbs that resemble staircases tilted sideways.
The first few miles were deceptive. Gentle rollers that curved through Los Altos Hills, under massive oaks whose limbs twisted above like ancient, arthritic arms reaching across the road. Redwoods stood farther back, tall and unbothered, while patches of eucalyptus filled the air with faint, minty notes that felt weirdly medical for a bike ride. Somewhere above, hawks circled lazily, scanning for rodents or perhaps slow cyclists who looked vulnerable.
We rolled past the homes of people who live very different lives. Gated estates, winding driveways, elaborate gardens with water features that seemed designed less for beauty and more for property tax inflation. I passed one mansion that had its own hillside vineyard because, apparently, buying wine is for amateurs.
Then the climbing began in earnest.
The supposed motor, technically capable of assisting up to 28 miles per hour, was much like an encouraging colleague who quietly backs out of the group project as soon as the heavy lifting begins. When the gradients hit double digits, the “e” in e-bike took on more of a philosophical role than a practical one. In short, it became heavy and the pedaling became thick.
Riders on featherweight road bikes passed me with a breezy cheerfulness that made me reconsider several of my life choices. One woman glided by with such alarming ease I half expected her to break into song. An older man—easily in his seventies—passed next, offering me an encouraging nod, which somehow made it both better and worse.
Eventually, I reached a rest stop—a small oasis manned by volunteers who, through some dark magic, were perky at this insanely early hour on a Sunday. Tables overflowed with orange slices, bananas, and a selection of gluten-packed cookies that I studied briefly, the way a monk might study a forbidden text: curious, wistful, and fully aware that touching them would end badly.
I met a man named Rob here, who asked if I’d take his picture next to his bike. I did, summoning every ounce of his phone’s untapped artistic potential. He returned the favor and, to his credit, managed to capture both me and my bike in the same frame—a photo skill not universally mastered by strangers. I ran into Rob again at the next stop, where he offered—unprompted—to take another photo of me. I politely declined and suggested a selfie instead, while quietly wondering if I had unknowingly signed up for some kind of awkward mid-life cycling portrait series.
The road pressed on, rolling up and down like some sort of poorly regulated carnival ride. The climbs reduced my world to the narrow strip of pavement ahead of my front wheel and the internal negotiation between my legs and lungs. The descents, when they came, were sharp, fast, and tinged with just enough danger to keep me hyper-alert. Shaded switchbacks flickered with dappled light, broken occasionally by deer grazing nearby who looked on as if amused by the entire concept of exercise.
Around mile 25, I briefly found myself riding near a man in a Roblox jersey—a wardrobe choice not typically seen on cycling routes. I assumed he worked for the company, or possibly had a child with very persuasive marketing skills. Or maybe this was simply his version of ironic humor—something to distract himself while his quadriceps screamed obscenities at him.
If The Sequoia was any indication, the ride across America wouldn’t just test my legs—it would also introduce me to an endless stream of strangers with odd habits, suspect fashion choices, and an inexplicable desire to photograph me mid-sweat.
By the time I hit the final stretch, the sun had climbed high enough to transform “pleasantly cool” into “mildly punishing.” My legs had entered that numb, resigned phase where they stop complaining and simply endure. The landscape opened up now and then, offering panoramic views of Silicon Valley—a glistening patchwork of tech headquarters, venture capital, and people who have assistants schedule their leisure activities.
I crossed the finish line alone. No fanfare. No banners. Just seven volunteers who clapped as though I had successfully loaded groceries into my trunk. Somewhere, a cowbell rang in what may have been encouragement—or sarcasm.
I found a folding chair and sat, carefully, because at a certain stage of fatigue, as I learned from my recent return to strength training, even sitting down can become a coordinated maneuver. My legs pulsed faintly with that familiar combination of accomplishment and looming regret. This was, after all, only 38 miles. The most climbing I’d ever done, but still just a small fraction of what waits for me if I’m actually going to cross the country on two wheels. Not once, but daily. For weeks.
It’s the kind of math that feels abstract when you’re sitting on your couch making plans. Less so when you’ve just finished your longest ride in two decades and your quadriceps are quietly filing grievances against your entire life plan. But still—I did it. I finished. I’m vertical. And somewhere in Rob’s phone, there are at least two pictures of me to prove it.