The eastern United States has three great drives run by the National Park Service: the Natchez Trace Parkway, the Blue Ridge Parkway, and Skyline Drive through Shenandoah National Park. After grinding almost 300 miles of freeway across Pennsylvania the day before, I was ready for Skyline Drive.
Winchester sent me off with 86° and humidity, a reminder that I was back in the South. Getting into Front Royal was slow going. At least I was finally seeing gas under $4 a gallon: $3.96 for regular, but $5.05 for premium. Whatever happened to premium costing 20 cents more than regular? More than a dollar a gallon feels like a cash grab.

Skyline Drive is beautiful pavement, and the speed limit is 35 miles an hour for all 105 miles. The rangers take that seriously. For the first hour, it was a gift. The views opened up at every overlook, and the fall color couldn’t make up its mind. Some trees were still green, some were just turning, and some had skipped straight past color to bare branches. I passed several bikes, all heading north, and never caught one at a stop. Somewhere along the way, a bug smacked me square in the chest, and when I stopped, a few of its friends were crawling around on the pavement. I’m pretty sure they were spotted lanternflies. They were first found in Pennsylvania in 2014, and Virginia’s first reported sighting was in Winchester, the town I’d left that morning. Apparently they’re making the same trip south that I am.







By the second hour, 35 miles an hour started to feel like a long time to cover not very many miles.





Because Skyline Drive runs through a national park, there aren’t many ways on or off, and lunch got away from me. By the time I realized I was hungry, every restaurant in the park was on its break between lunch and dinner. I finally found the New Market Taproom at Big Meadows. The pizza was average. Cell service was worse, so I wandered the property until I found enough signal to join a meeting. I’ve been doing some work with the Nightscout Foundation. Diabetes is important to me, and I like their mission, so I gave them the afternoon.


Dad and I had missed each other on his birthday. We’d traded texts, but every time he was free I was busy, and every time I was free he was busy. At about 5:15, I called him from the parking lot at Big Meadows. Golden hour was just starting to come through the trees.

We talked for about 20 minutes, one of our first real conversations since the trip began. He asked where I was. He’d pictured me farther south, in the Smokies. To be fair, I didn’t have a good sense of Shenandoah either until I started planning this trip in detail. He and Mom have been getting the postcards, and they both enjoy them. A few of the recent ones haven’t arrived yet, so I got to tell him about places he hasn’t seen in the mail. The postcards are always a few states behind me. We spent most of the call on Rhode Island. My sister had recommended it, and Dad was glad I’d gone to see the mansions in Newport. We both marveled at how grandiose they were. I think he was a little surprised I went. Honestly, so was I.



By the time we hung up, the light was going. I’d ridden about two-thirds of Skyline Drive, and I bailed on the rest. I didn’t want to get stuck up there in the dark. It was a trade, and I knew it when I made it.








The Grey Pine Lodge in Waynesboro sits down in a valley off the side of the road, and I almost rode past it. The property wasn’t well lit, so I fished my luggage out of the bike’s various pockets mostly by feel. There were fire pits scattered around, mostly hidden in the darkness. Nobody was on site. It didn’t feel homey until I got around to the back, up the stairs, and into my room, which turned out to be really well done.
Corey from Washington used to live in Virginia, and he told me the best people in the entire state live in this area. He was emphatic about Blue Mountain Brewery in Afton, Nelson County’s first craft brewery.
That created a problem. Many years ago, I promised my mother I wouldn’t drink and ride. It was hard enough for her to wrap her head around her son riding a motorcycle at all, and I’d read enough, including the Hurt Report‘s finding that alcohol was involved in almost half of fatal motorcycle crashes, to know she wasn’t wrong to worry. Usually keeping that promise means parking the bike and walking to dinner, or skipping the beer. There was no walking from the Grey Pine Lodge, and ordering a Diet Coke at the brewery Corey had talked up felt wrong. I wasn’t sure I’d find a rideshare in a small town at night, but I took the chance and called an Uber.
I sat down near a big post at the bar, one empty chair away from Jack. He was about 30, lanky, with a natural smile and a decidedly blue-collar look: an oil-and-gas t-shirt from a company I didn’t recognize, work jeans, and boots. I started the conversation (I’m trying to get better at that), and it came easily. He’s a carpenter by trade, a bit of a jack of all trades (no pun intended), and he wants to get more into sustainability. I tried to ask enough questions to keep the conversation going without turning it into an interview. He was watching the Brewers and the Dodgers in the NLCS and rooting against LA (aren’t we all?). He doesn’t like the Dodgers, but he gives them credit for the strategy behind their last World Series win. Baseball, he told me, is a game of strategy. You can’t just hit a home run and win it like you can in other sports.

On the other side of the post sat a couple who had just moved up from Atlanta after 35 years. Their son is at UVA, and they wanted to be closer to him. They’d had enough of the growth and the traffic. I’ve seen Atlanta get more walkable from the city side, but from the suburbs I get it. I’ve passed through a lot of small towns on this trip, and it has me wondering where I want to be next. Maybe somewhere more rural. Maybe somewhere decidedly urban, like my time in Vancouver, where walking was how I got places. I don’t think San Francisco is that city, but it’s something I’m considering.
Corey had recommended the pumpkin beer, and he nailed it. Spooky is an imperial pumpkin ale, and in a season that’s somewhat hostile toward pumpkin spice, Blue Mountain delivered. As I was heading out, somebody mentioned it was going to rain tomorrow. Ugh. I didn’t see that coming.


The Uber driver couldn’t find the hotel, so I talked him down into the valley from the back seat. The fire pits were still dark when we pulled in, and I was surprised at how little I’d done that day, and how much. I hadn’t finished Skyline Drive. But I’d talked with Dad, given an afternoon to something I care about, and enjoyed a good beer without breaking my promise to Mom. I’d make that trade again.
Ride Details
Route Map
Start
Winchester, VA
Destination
Waynesboro, VA
Distance
Approx. 128 miles
The Ride at a Glance
Scenery
★★★★★
Curves
★★★★☆
Road Surface
★★★★★
Traffic
★★☆☆☆
Difficulty
★★☆☆☆






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