Three Decades and Going Strong

524-Mile Walk Across Virginia Sparks a Lifelong Passion

Article by Jeffrey H. Ryan

Photography by Jeffrey H. Ryan

Originally published in Leesburg Lifestyle

Growing up in Maine meant that my first impression of Virginia was through the back window of a 1969 Ford Torino station wagon rolling toward Williamsburg. My parents were adamant about immersing their children in history, which paid immediate dividends – what 12-year-old could ever forget forging a nail while being expertly guided by a blacksmith wearing colonial garb? — and still inform my writing today.

Twenty-three years after that family vacation, I returned. This time, I would experience Virginia at an average speed of 3 miles-per-hour. My good friend, Wayne Cyr and I were six years into a twenty-eight-year quest to complete the Appalachian Trail in sections when we made the 106-mile walk from Waynesboro to Front Royal — an end-to-ender through Shenandoah National Park.

Thanks to its diagonal route stretching from Maine to Georgia, more than one-quarter of the 2,100+ mile Appalachian Trail lies within Virginia. Wayne and I walked every one of them over five trips between 1991 and 2004. 

The way we hiked the trail wasn't sequential or contiguous. We seldom picked up where we left off. This was by happenstance at first, then became a recognized and honored aspect of how we rolled. Every winter, Wayne, who lived in the Hartford, Connecticut, area at the time, and I, a native of Portland, Maine, would set about choosing that year’s destination, based on projected time off and factoring in travel time to and from the section in question. It wasn’t long into our adventure before Wayne, an analyst by trade, identified Virginia as a multi-year endeavor. Realizing it would take at least five trips of 10 to 14 days each, we jumped aboard a southbound Amtrak train in 1991 to get started.

An Unexpected Commute 

People often ask why we didn’t drive to the trail. It’s a great question. We decided that, with only limited time off each year to hike, we didn’t want to have to get off the trail then somehow get back to where we had parked. It ended up being easier to use a combination of public transportation and private shuttles: people who would take hikers to and from the trail for a fee. There was no such thing as Uber back then.

On May 22, 1991, at 2:00 a.m., we stepped off a bus in Waynesboro and started walking toward Skyline Drive. It didn’t take long to realize what a dumb idea this was. By luck, an abandoned gas station appeared on our right. We scrambled behind it, laid out our ground pads and took a four-hour nap. At first light, we packed up and got back on the road. Literally, fifteen seconds later, the man who lived across the street came over to ask if we wanted a ride to the trail. 

Walking Across VA by the Numbers


Waynesboro to Front Royal

May 22 – June 1

106.6 miles


Rockfish Gap to Daleville

September 9 – 22

133.8 miles


Daleville to Bland

October 10 – 23

128.1 miles


Bland to Damascus

September 24 – October 4

120.7 miles


Harpers Ferry to Front Royal

December 16 – December 22

52.42 miles

“It’s no trouble, I’ll be right back,” he said, introducing himself as “Jack.” Jack disappeared behind his house and reappeared wearing a giant grin and driving a hearse. “Should be plenty of room in here,” he said.

Jack got a big chuckle out of us. The shocked look on my face when he appeared in the hearse had been just the response to get us bantering for the whole ride. He dropped us off at the now defunct Howard Johnson’s in Rockfish Gap, where we ceremoniously stepped out of the hearse and bellied up to the breakfast bar.

The rest of that hike was a testament to the naiveté of a couple of New Englanders thinking that the late May temps in the mountains of Virginia would emulate those at home. Instead, it was oppressively hot and humid the whole way. It was still a wonderful trip — filled with memories and punctuated by the need to plan each day around water management. But from then on, our Virginia trips would be in October or later. 

Four More Visits — Four Hundred More Miles

Our other Virginia trips on the AT took place in 1993, 1997, 2003, and 2004 (See sidebar). That last trip was the latest we would make in our 28-year journey, wrapping up on December 22nd and hitting a New England-ish 13-degree overnight low along the way.

There were so many good times — too many to recount here. One marvelous thing about doing a long-distance trail in sections is that every trip yields its own insights and rewards. But one overarching theme took hold: I was compelled to revisit Virginia to hike and for other reasons that the ensuing years would reveal. 

The Trail Leads Back

Ten years after my last Appalachian Trail hike in Virginia, I finally made it back. My intention was to camp in Shenandoah National Park, take photographs and work on the book about my 28-year hike that would eventually become Appalachian Odyssey: A 28-year Hike on America’s Trail. That plan was scuttled when a friend offered her family’s otherwise unoccupied 1812 farmhouse in Strasburg for me to use for ten days.

From the moment I got done fumbling in the dark, turned an antique key in the lock and swung open the door, I had an inkling that I’d walked into the ideal spot to write. Waking up to a view of working fields with the northern Shenandoah range rising above sealed the deal. Thanks to my friend Martha’s generosity, that magical farm became my writing refuge and hiking basecamp for the next seven years. It was my great fortune to turn that antique key in the front door lock after appearances at The Smithsonian and lectures in Front Royal, Luray, Charlottesville, Stevens City, Winchester and Harrisonburg. (Sipping coffee on the porch and gazing at Signal Knob while being interviewed for a Perth, Australia podcast is another indelible memory.) 

Then, of course, there was the hiking. You can’t spend days looking at Signal Knob without wanting to scramble to the top. It was especially fitting that my friend Art and I had pre-orchestrated an experiment whereby he would try to signal me with a giant flashlight from the farm during broad daylight. (I was dubious, but it worked, thus the mountain lived up to its name again.) The Tuscarora Trail and Massanutten Trail also became favorite haunts as my writing and hiking lives intersected at last.

The farm in Strasburg was sold in 2020, but my hiking and writing affair with Virginia lives on. I tucked myself away in Abingdon for two weeks in 2021 to fine-tune the manuscript for my latest book, “This Land Was Saved for You and Me.” I have my sights set on another mountain community as my next source of solitude and inspiration. Yes, there’s something afoot between Virginia and me. I only needed to walk around a while to discover it.

About the Author

Maine-based author and speaker Jeffrey H. Ryan has a passion for exploring the outdoors on foot and along the dusty paths of history. His travels on thousands of miles on both America’s most famous and lesser-known trails have inspired several books including Appalachian Odyssey and his 2022 hardcover, “This Land Was Saved for You and Me.” When he is not researching and writing, Ryan can be found exploring the backroads of the USA and Canada in his vintage 1985 VW camper.

He will be the featured speaker, Friday, June 9th in the town of Hillsboro’s Eat, Drink and Be Literary event at the Old Stone School. The following day, June 10th, Jeffrey will be at the same venue for the Appalachian Trail Festival in The Gap — an all-day event featuring live music on The Gap Stage, dozens of vendors featuring hiking and outdoor goods, speakers and demonstrations, food, local beer and wines. His books will be available for purchase and signing at both events.

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