I had envisioned this day so many times over the past few months. It was supposed to be thrilling—the beginning of something monumental, an escape from the mundane and a leap into adventure. Instead, I was annoyed by my inability to sleep, my mind buzzing with a nervous energy while my heart thudded in anticipation of the trip ahead.

The apartment however, was quiet, and I tried to tiptoe around without waking Alyssa as I made trip after trip downstairs with my gear. I had spent the past several months purchasing anything I thought I might need for the adventure ahead, and while I obsessively planned, she sat by patiently—jealous at times, worried at others. The least I could do was to let her get a few more minutes of sleep.

Once my panniers were full, and everything else had been strapped to the back seat of my Triumph motorcycle, I headed inside one last time to kiss Alyssa goodbye. She squeezed me tight, as if silently pleading for me to stay, and for a brief moment her grip made me hesitate. As much as she supported me, I knew she worried. I felt a pang, not of guilt exactly, but of realization. This was real, and I felt the weight of competing emotions as the fear of leaving the comfort of home fought against the excitement of the freedom that lay ahead.

Driving out of the apartment complex felt surreal and I chuckled to myself as I passed by those idling in the morning commute. I was free while they were all trapped, confined to their cars, stuck in the traffic, and enslaved by their jobs. The irony was short-lived, however, as my gear—so carefully packed and secured—began slipping off the bike less than a mile down the road. Annoyed, I pulled over to readjust everything, those same commuters now slowly passing me. Uncertainty started to creep in: If I’m already having problems now, how can I make it when I’m in the middle of nowhere?

The stops continued over the next couple of hours. Whenever I thought I had my gear situation figured out, something would throw it into disarray. As I wrestled with my belongings, continuously readjusting my setup, I became determined not to let my spirits dampen, instead thinking about the story these mishaps would tell.

Eventually, the sense of adventure returned as I made my way through the winding roads of Virginia's Appalachian foothills. Pushing the loaded bike into each turn, the road felt like it was made for riding. It seemed strange to be out here alone, when so much of what I was doing something I would have wanted to share. The best I could do was to make frequent stops for photos, either of a road or an occasional farmhouse, anything that might capture the magic of the place and the moment, each shot feeling like a way to mark my progress, and I imagined how Alyssa might respond each time I clicked the shutter.

Pavement turned to gravel as I followed the purple line on my GPS. With the unfamiliar weight of the extra gear, I drove more carefully than normal on the loose rocks, but soon felt my foot sinking further and further with each press of the rear brake. Once again I found myself stopped on the side of the road, this time discovering a leak at the top of the brake caliper. I had tools and I had spare tubes for my tires, but I didn’t have any spare brake fluid. I torqued down what I could and hoped for the best, certain of an easy fix once in town.

Barely a half hour later, my bike skidded over a patch of loose rocks and before I knew it, the Scrambler and I were both on the ground. My heart sank as I assessed the situation, though it wasn’t as bad as it seemed. The bike and I were both fine and, after a bit of effort, back upright and on the road once more, doubt building in my mind again.

I continued onwards, the overcast sky starting to look like rain as the evening approached, and I began to realize an uncomfortable truth: all of the unintended stops—to readjust my gear, to take photos, to pick up the bike after my fall—had delayed me more than I planned. I didn't want to ride in the dark but, even making a beeline on the interstate, I wouldn't arrive at my hotel before night fell. But adventures often don't go as planned, and I had to realize that this journey wasn’t just about the riding—it was about adapting and learning to handle whatever came my way.  

Night came, and I was still several miles from Boone when the weather finally turned, the clouds low and full of rain. As the mountain roads climbed and dipped, I could barely see more than a few feet in front of me. The only indication of where the twist road went came from the lights of the vehicle ahead of me. I used them like a lifeline, tailgating behind them closer than was safe, but I felt it was better than the alternative, imagining myself careening off a mountain cliff if I made a mistake. When I finally rolled into the city, I was soaked and exhausted, feeling the weight of every mile I had covered.

Even then, the day wasn’t over. I realized I had only plotted my route to the city, not to my hotel. I pulled under a bank overhang to get the hotel's address from my phone, only to find water dripping from its casing. With my phone dead, I had to go off my memory and whatever listings were in my GPS.

Finding something that felt right, I headed back into the rain, only to drop the bike again, this time in the middle of a 4-way intersection. With cars staring at me and adrenaline pumping, I picked the bike up as if it weighed nothing, a challenge that should’ve been made harder by the wet pavement. A broken footpeg lay in the street. I picked it up from the asphalt and placed in my jacket pocket, then limped the bike to the hotel, a fitting end to a day where nothing had gone quite as planned.

Of course, I had planned to be in Asheville in time for a 10 a.m. tour at the Biltmore Estate. Since that was still a two-hour ride away, and repairs still needed before I could set off, I set my alarm for much earlier than I wanted: 5:30 a.m.

Wearing nearly all of my gear in hopes of staying warm, I went outside to find the Scrambler still under the hotel’s overhang, safe in the pre-dawn rain. The foot peg fix was quick, simply replacing it with the rear peg. It wasn’t a perfect replacement, but it would work and I wouldn't be riding with a passenger during this trip anyways.

The brake was another matter. While bleeding the system, I ran out of brake fluid and, with no stores open that early in the morning, I could only piece the bike back together and hope for the best, planning to fix it once I arrived in Asheville.

As I rode out into the fog-covered mountains, each turn revealed a breathtaking valley draped in mist. I longed to stop and photograph it, but the clock was ticking, and I already doubted I could make it to the Biltmore in time. Besides, I was already down several cameras—a GoPro had fallen off the bike at some point early in the day before, my helmet cam’s charging cable had melted on the exhaust, and my cell phone had drowned in the rain. I was frustrated at the moments I couldn’t capture, but I tried to remind myself that it was okay for some things to be left as a memory.

I pulled into the Biltmore parking lot a few minutes past 10. Still in full riding gear, I rushed inside hoping to reschedule. With the poor weather, I had no issues with availability for the next Rooftop Tour. The rain started again while I waited, the gray sky and steady downpour providing a moody backdrop to the classical architecture of the mansion. It was as impressive of a structure as I had remembered from my visits as a kid, but I felt more aware of the details now as an adult.

We wandered through the house, climbing stairways and traversing through the various hallways. A few of us would step onto the rooftop, where I quickly snapped few photos before the cold rain made us escape back into the comfort of the house. This would be one more thing that would be remembered more than it would be captured.

The tour ended and, though part of me wished I could have seen more, I left the mansion feeling a sense of accomplishment. I rode through the estate’s scenic grounds, narrowly avoiding a territorial goose. After a quick stop at McDonald’s—oddly with a grand piano playing covers of pop songs—I decided to stay in Asheville for the night. I was cold and tired, the bike still needed repairs, and I still needed to replace my phone.

After checking into a hotel and running my errands, the rain had stopped, only to be replaced by snowflakes. By the time I finished my repairs, my hands were shaking from the cold, but it was fixed and I was ready to get back on schedule.