
Motorcycling is a study in contradictions: the heat of the engine against the chill of mountain air, and the silence of the high ridge versus the pulse of the valley below. To ride the roads of Skyline Drive and the Shenandoah Valley in Virginia is to live in these dualities.
From the saddle of my silver 2007 Triumph Bonneville, I set out to test both ends of the spectrum, riding a 200-mile loop up all 105 miles of Skyline Drive, and back down through the valley below, hoping to see both sides of this slice of motorcycling heaven.
I start my ride a few miles from my home, inside Shredders BBQ in Waynesboro, with a hearty breakfast of brisket and eggs. If you have never had BBQ for breakfast, you are missing one of life’s simple pleasures. This veteran-owned smokehouse caters to families and bikers alike. On previous visits, my favorite meal has always been the Cheesy Greaser.

“I invented that sandwich in my food truck days,” said owner Michelle Pack. “I really wanted a grilled cheese, then I added BBQ pork, melted cheese, and the pickled onions to really set it off.”
That sandwich, served on Texas toast, is the perfect pre- or post-ride meal.
I leave Shredders full and happy, and head toward Skyline Drive. The three-mile climb up Three Notched Mountain Highway averages an 8% grade, warming up both the bike and my senses. After passing through the gates of Shenandoah National Park, I settle into the rhythm of the mountains. Every overlook seemed determined to outdo the last. Layers of blue mountains dissolved into the horizon while red-tailed hawks rode invisible currents below eye level. I see chipmunks scurry across the road and fleeting glimpses of black bears hurrying into the treeline. The feeling of freedom brings a smile to my face that stays for the rest of the ride.
The pace here is deliberate. At 35 mph, Skyline Drive is more of a scenic cruise than a technical attack. I think of those famous dragonesque motorcycle roads like the Back of the Dragon or the Claw of the Dragon. Skyline Drive is sometimes called “the 35” due to its strict 35 mph speed limit. I have always thought this great motorcycling road needs a better publicist. Lying farther north than other parts of the Dragon’s body, I wonder what draconian name this road has earned. Given the panoramic views looking far to both east and west, I decide on a better name: The Eye of the Dragon.

The predictable curves and smooth pavement of the “Eye” offer the perfect opportunity to practice the skills my dad taught me when I first started riding as a teenager. On those rides, my dad shared with me the wisdom of looking deep into the turn and hugging the white line on blind turns to avoid oncoming cars. Every smooth corner I turn reminds me that his best lesson wasn’t about motorcycles; it was about judgment. I can proudly report to my father that I did not cross the white or yellow lines once for 105 miles.
OK, that’s not entirely true. I touch paint twice. The first time, I pass a white-knuckled driver with a flat state license plate going 20 mph under the speed limit. The second time is when I pull in to get water at Big Meadows, the spiritual halfway point of the Skyline. Here, at the restaurant that coincidentally has the only place to get gas inside the park, I meet a rider from Charlottesville named Eric Ziders. He is riding the entire length of Skyline Drive in a single day, a 100-mile feat known among our two-wheeled cousins as a “century.” After a quick mental search for the right word, I ask if he plans to attempt a bicentennial, a 200-mile ride in a day, or as appropriate for this year, a semiquincentennial (250) anytime soon.
“I have family picking me up from Front Royal later tonight,” he said seemingly baffled by my question.

The next 50 miles of Skyline Drive matches the sublimity of the first. A few minutes after leaving Big Meadows, the road rewards me with an absolute ripper of an ascending left turn. The 360-degree parallel twin in my Bonneville was upgraded in 2007 from 790 to 865cc, and the extra umph sings in my ears. Halfway through the sweep, a U.S. Park Service truck appears, sitting halfway in my lane. Luckily, those 25-year-old riding habits keep me completely out of danger. A few miles later, I roar through a tunnel, blipping the throttle, honking the horn, and yodeling the whole way.
Early explorers viewed the Blue Ridge as the final wall of the frontier, a daunting barrier to everything further west. Observing the endless overlooks on Skyline Drive, I realize these people didn’t stop at the Appalachians because they were cowards. They stopped because they found exactly what they were looking for. Today’s riders are no different. We’re still chasing that same elusive sense of freedom these settlers found centuries ago.
After a little over three hours, I finish my Eye of the Dragon. Many riders would simply turn around and head back the way they came, but that would mean missing the other half of the story. Highway 340 runs down the west side of the mountains back to Waynesboro, trading overlooks and forests for streams, farmland, historic churches, and small towns content to let interstate traffic hurry along elsewhere. Front Royal, the northern terminus of Skyline Drive, boasts a thriving, walkable downtown decorated with flags and hanging baskets, looking like a scene straight out of the movie “Pleasantville.” I text a picture of the gazebo on Main Street to my daughter, and she tells me it looks like Stars Hollow from “Gilmore Girls.” I’ll trust her on that one.

“All roads lead to Front Royal,” exclaimed Lizzie Lewis, the community development and tourism director for Front Royal. Describing the easy-to-get-to town, reachable by interstates 66 and 81, as well as highways 522, 240, and Skyline Drive, it is no wonder Front Royal is a great starting or ending point for motorcyclists across the East Coast.
“We will feed you even if you aren’t hungry. We have a pool hall and an arcade, and the Virginia Beer Museum is a great stop to learn about something most of us are interested in,” she said. Lewis also lets me in on another hot tip: in partnership with the DawgHouse podcast, a motorcycle podcast produced by other members of the Front Royal tourism office, Front Royal has created specially curated routes for motorcyclists through the surrounding countryside. These rides show mileage, points of interest, places to take awesome photos of you and your bike and are viewable at www.discoverfrontroyal.com.

After an excellent lunch at Vibrissa Brewing in Front Royal, I point the bike south toward Luray. From this point on, the ride shifts from the meditative, slow-motion observation of the Skyway into an exercise in situational awareness. The highway opens up into a 55-mph dual road, and the towns blur into a rhythmic montage of the Shenandoah Valley’s living history. Yet, to say this isn’t the Blue Ridge would be wrong. The people in these communities, whose ancestors crossed the ridges centuries ago, are shaped just as deeply by the quiet forests and rivers as the people who live on tree-shaded back roads.
Luray, the seat of Page County, is famously anchored by its subterranean wonders, and its town center remains a classic mountain-valley hub. Here, the architecture reflects a mid-19th-century boom stemming from the discovery of Luray Caverns and the addition of a railroad in 1881. I pause for a moment at Broad Porch Coffee to enjoy the atmosphere before heading out on a mileage-adding side quest.

Heading west on Business 211, I discover Cooters, which offers a completely different vibe. Cooters is a “Dukes of Hazzard” museum, gift shop, and restaurant. In the parking lot, a replica General Lee gives passenger rides up and down the road. Inside, a live band plays Lynyrd Skynyrd’s “The Breeze.” This is also the America I love.
Leaving Cooters, I keep west and then cut south back onto 340. On Skyline Drive, I could have left fourth and fifth gear at home without consequence. On this highway, I constantly search for a sixth gear. Instead of practicing cornering skills, I rely on a different survival instinct: assuming I am completely invisible to every driver on the road.
Still, I refuse to let the faster pace blur the journey. Every few miles, more great sights and small towns float into view. I pass community ballfields adjacent to cornfields, and white houses topped with red or silver metal roofs, the first denoting money, the latter whispering of roots. The speed of the Bonnie feels entirely at odds with the deliberate pace of the land and its people.
The Shenandoah Valley Railroad, which travels at the western base of the Blue Ridge, was completed in 1881 and linked the ore-rich deposits of the Blue Ridge Mountains with Roanoke to the south and Hagerstown, Maryland to the north. Most of the towns on Highway 340 got their kickstart by being stops along this important connector of the south’s riches to northern industrial areas. As I roll through Shenandoah, I pass a duckpin bowling alley and the Lutheran Church founded in 1733, then detour to an antique car show packed with classic Corvettes.

By 1890, the railroad was sold under foreclosure to Norfolk and Western Railroad, which, after merging into Norfolk Southern, continues to operate to this day. Continuing south on 340, I soon find myself racing one of these trains where the tracks parallel the road. It wasn’t a fair contest. I clocked the locomotive at exactly 32 mph. Feeling its pain, I recall the strict 35-mph limit on Skyline Drive.
Further down the road in Elkton, the valley shares another unique geological gift. When Molson-Coors looked to expand its operations east of the Mississippi in the 1980s, they chose Elkton because its limestone-filtered water closely mirrors the water at their original plant in Golden, Colorado. It pays to be friends with the workers there. They get a few free cases a week to share with whomever they like. Burt Reynolds would have loved it here.
The mid-afternoon brings a sudden shift in the atmosphere. By the time I hit Grottoes, the mountains begin casting long, cool shadows across the road. Just as I pass Grand Caverns, the oldest continuously operating show cave in the United States, a fierce thunderstorm breaks. The sky turns a bruised purple, the air grows heavy with the scent of ozone, and the temperature drops. My mission instantly shifts from scenery-watching to survival mode as I push through the deluge, upgrading my trip to “type 3 fun.”
I had planned to finish the day with a cold beer at Basic City Brewing in Waynesboro, just a mile from where I started at Shredders. The weather, however, has other plans. Oh well, there is cold beer and dry clothing at home.
Twenty-five years ago, I believed motorcycles were about speed. Today, I know they are about the stories waiting inside roadside barbecue joints, conversations at visitor centers, and cyclists chasing a century. These stories live in old churches, forgotten railway towns, mountain overlooks, sudden thunderstorms, and winding backroads.
Somewhere along the ride, I stop thinking about the irony of riding a British motorcycle through American roads on the 250th anniversary of the nation’s founding. Freedom isn’t built into the badge on the fuel tank. It is found in the places a motorcycle can take you, and in the people you meet once you get there.
That’s a ride worth repeating.


