I woke up at Deals Gap with the previous evening’s advice still in my ears.

Everyone, and I mean EVERYONE, had told me the same thing. You ride the Tail of the Dragon because you have to, but the Cherohala Skyway is the better road. I’d ridden the Dragon the day before, and I was curious whether the Skyway could live up to all that enthusiasm. I headed down US 129 toward Robbinsville and picked up NC 143 toward Santeetlah Gap, where the Skyway begins on the North Carolina side.
They were right. The Cherohala Skyway was exactly the kind of road I love to ride. It reminded me of Skyline Boulevard on the San Francisco Peninsula, heading south into the Santa Cruz Mountains. What makes both roads special is their balance. There are long, fast sweepers where the bike settles into a rhythm, tighter technical corners that can sneak up on you if you’re not paying attention, and enough straightaways to relax a little and take in the scenery. The Skyway had all of that, and because so much of it runs above 5,000 feet, the views were wide open, with nothing to stop you from seeing everything below.

The speed limit is 45 on the North Carolina side and 40 in Tennessee, compared with 30 on the Dragon. The pavement was better, the traffic was lighter, and there was more room along the edges. There were also pull-offs every few miles. The Dragon demands your attention almost continuously, and there aren’t many places to pull off without finding a photographer waiting for you. The Skyway still expects good motorcycling discipline, but it also gives you room to enjoy everything left and right of the curves, too.





For much of this trip, I’d been chasing fall color, watching the season work its way north to south, alpine (whatever alpine there is here) to valley. On the Cherohala Skyway, something had changed. The trees weren’t just turning anymore. Many had already dropped their leaves. A new term had entered this ride’s vernacular: past peak.


Up at the higher elevations, above 5,000 feet, there wasn’t much color left to chase. The ridgelines were bare, and the trees stood without a single leaf. A week earlier, I’d been enjoying the fall color along the Blue Ridge Parkway. Up here, the show had already ended.



The lower elevations were another story. There were still pockets of yellow and gold, and I found myself stopping frequently to photograph the contrast between the bare mountains above and the trees that were still hanging on farther down. This was one of the things I liked most about the Skyway. I could enjoy the technical riding for a while, find a pull-off, get the camera out, and then go back to riding. I never felt like I had to choose between the road and the scenery. The road design felt like California again.
About halfway across, an aggressive rider came up behind me and passed me. I let him go. It’s no sweat off my skin. About an hour later, after riders coming the other direction tapped the top of their helmet signaling police, I came around a bend and found him on the shoulder with a cop parked behind him – lights in full display. I’ll admit I enjoyed that a little more than I should have due to the aggressive pass on a somewhat empty road.
I came down into Tellico Plains and headed straight for the Cherohala Skyway Visitor Center and museum. I had one particular thing to accomplish while I was in town. Tennessee was the final state in my Appalachian Trail stamp series, and I wasn’t leaving without a postcard.
I secured a beautiful postcard of the Skyway. Score! Then came lunch. I asked AI where to eat, and it recommended Iron Works Grille. Unfortunately, Iron Works was about a mile back up the Skyway, and I wasn’t particularly interested in backtracking. I asked again for something along my route. AI offered a couple of alternatives, but it really wanted me to go to Iron Works. I found myself arguing with my phone about where to have lunch, which seemed a little ridiculous fighting with an AI bot over a mile, so I finally gave in.

As it turned out, AI was right.
When I walked into Iron Works, Jim and Gene spotted me almost immediately. They called out my name, reached over to shake my hand, and pulled me into their booth’s conversation. I’d met them two nights earlier at Two Wheels of Suches, and here we were again, sitting in a restaurant in Tennessee completely by happenstance.


One of the unexpected pleasures of this trip has been discovering that I’m starting to know people back east. I’ve found something similar in Savannah with the Kickstart Vintage Motorcycle Club. These aren’t just strangers I’ve had a conversation with at a gas station or a restaurant. They’re people I recognize now, and people I’m beginning to look forward to seeing again. I’ve spent years building a community of riders out west, and I hadn’t really expected to find the beginnings of another one over here so quickly.

In the next booth sat Roland, the Mississippi rider I’d met the night before. We’d already had our conversation at Deals Gap, and he seemed to have mellowed out since, so I was happy to let him enjoy his lunch in peace. He never saw me come in, and he didn’t see me on his way out either. Sometimes meeting people goes that way, and it’s all good.
Jim and Gene, however, had strong opinions about how I should get to Birmingham.
“Man, you can’t take the freeway,” they said. “There’s so much good on Highway 411. You’ll go through more of Georgia.”

“Oh yeah,” I said. “That goes through Rome.”
They talked up the small towns, the relaxed pace, and the fact that the route would only add about 45 minutes. Under normal circumstances, they wouldn’t have needed to convince me. I’d spent weeks taking the more interesting road whenever I could, and Highway 411 sounded like exactly the kind of riding I’d been enjoying.


Unfortunately, I had a job interview scheduled that afternoon. Someone had reached out about an opportunity, and I was interested enough to have the conversation. I needed to find somewhere with a reliable cell signal, and I wasn’t interested in being stranded on a two-lane highway in a dead zone when the call came through. For once, the freeway was the better choice, even if it wasn’t the better ride.
After Jim and Gene left, I stayed in the booth and wrote out my postcards. Some were thank-you notes to people who had helped me along the way, and one was the last Appalachian Trail postcard to Dad. I’d started the trip with a sheet of stamps representing the states along the trail, and I’d been working my way through them as I traveled. Some postcards had been easy to find. Others had turned into surprisingly difficult little scavenger hunts. I’d carried the stamps and postcards around for weeks, looking for places to write them and post offices where I could send them.
Atlanta was still ahead of me, and I’d decided to send one more postcard from there because it was where Dad and I grew up. That would be the closer for the larger journey. But Tennessee was the last of the Appalachian Trail stamps, and finishing that series mattered to me. At the Tellico Plains post office, I peeled the Tennessee stamp off the sheet. It was the last one, and suddenly I was holding an empty sheet of Appalachian Trail stamps. This part of the journey was done.


I handed the stack of postcards to the man behind the counter.
“These are regular outgoing mail,” I told him. “This one is special, though. It’s the last in a series of postcards to my father, one from every state in your Appalachian Trail stamp series, plus a few more. Please handle this one with care.”
He smiled. “You got it, man.” He understood what I was doing. I suspect I wasn’t the first motorcyclist coming into this post office with a story.
He didn’t drop it in the bin with the others. He carried it into the back to be handled on its own.

Outside, I was trying to take a picture of myself with the phone when a woman in her thirties stopped and asked, “Do you mind if I take your picture?”
“Of course not,” I said, and I handed her the phone. “This is the last postcard in a series to my father. Tennessee is the last state I needed to finish the Appalachian Trail stamp series.”
She smiled and took the picture, happy to be part of it. I hadn’t expected a visit to the post office to become one of the more memorable stops of the day, but that’s how this trip has gone sometimes.
Something welled up in me as I walked out, and the only word I have for it is humility and pride. I’d set out to do something for Dad, and I’d followed it through across thousands of miles and more than a few states where finding a postcard had become an adventure of its own. I still had Atlanta ahead of me, but I was holding the empty stamp sheet, and that felt pretty good.
The rest of the afternoon was interstate riding, and it was a pretty abrupt change from the Cherohala Skyway. I took I-75 toward Chattanooga, where I-75, I-24, and I-59 seem determined to dump all their traffic into the same place. Add construction to the mix, and the traffic was rough. After spending the morning enjoying the curves and scenery of the Skyway, I was back to watching brake lights and tractor-trailers.
Somewhere along the way, I pulled into an interstate rest stop to take the interview. I couldn’t think of anywhere better to do it, which is one of the practical complications of trying to conduct a job search while traveling around the country on a motorcycle. I was interested in the opportunity, but I wasn’t entirely sure what I wanted to come of the conversation. I can feel the tension between enjoying this time away and knowing that, eventually, I need to decide what comes next.
I’m not sure I’m ready to go back, and I’m not sure yet what I’m going back to. Sitting at a rest stop beside the freeway wasn’t where I’d imagined having a conversation about my professional future, but I had a solid signal and enough time to make the call. For now, that would have to do.

Georgia actually provided a little relief once I got onto I-59. It’s more of a secondary interstate than I-75 or I-24, and the truck traffic thinned out enough that I could settle back into the ride. Alabama, however, was quick to put an end to that. Deep potholes, rough pavement, and lane closures pushed traffic well onto the dirty shoulder. None of that was particularly enjoyable on a motorcycle, especially one loaded for a long trip. I found myself paying close attention to the pavement and looking forward to getting off the freeway.
I was particularly glad I wasn’t riding that stretch after dark. Crossing into Central Time had given me an extra hour on the clock, but northeastern Alabama sits so far east in the time zone that the sun seemed determined to take it right back. It reminded me of riding I-95 in Maine, way over on the eastern edge of the Eastern Time Zone, where evening seemed to arrive much earlier than I expected. Changing the clock doesn’t change where the sun is in the sky, and the daylight was disappearing faster than I would have liked.
D was waiting for me in Birmingham. When I told D and his partner K about the construction, K laughed and said that freeway had been under construction for at least 40 years. He noted that he remembered traveling between Birmingham and Fort Payne growing up, and swore something on that highway has been under construction his entire life. I guess Alabama has decided that finishing I-59 would spoil a perfectly good tradition.
Ultimately, I wanted to see D’s pool. He’d poured a year of hard work into it, and I wanted to be there for his moment, even with winter nipping a the door. Usiders do things like this. We show up for each other, even when it means a few hundred miles out of the way. It was already dark, but the pool was glimmering against the night sky, the water 65°, and the air a touch colder. I wanted to jump in, but we both knew that moment had passed. Like the trees on the Skyway that morning, the pool water was past peak. D’s work wasn’t. It was still worth the ride.
Next summer I’m jumping in.
Ride Details (Skyway)
Route Map
Start
Deals Gap, NC
Destination
Birmingham, AL
Distance
282 miles
The Ride at a Glance
Scenery
★★★★☆
Curves
★★★★☆
Road Surface
★★★★☆
Traffic
★★★★★
Difficulty
★★☆☆☆






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