This Substack section is dedicated to a trip I took on Route 66 from Chicago to Santa Monica between 2017 and 2018, with a detour through Alaska, the Yukon, and Canada, which will inevitably become its own story in the future. Along the way, I share my photos, the history of the road, and my personal story of riding with my friend Mark, a fellow motorcyclist who developed Multiple Sclerosis and could no longer ride. Since I plan to ride the route again for the 100th anniversary in 2026 with my daughter, Sophia, now seems like a good time to revisit my experience.
Today, most people see Route 66 as a symbol of a bygone era, with old cars, diners, and quirky roadside attractions. Few realize its complex history. Time alters our perception of reality, and nostalgia often takes over for truth. But whether you're curious about the road’s history or just craving adventure, Route 66 still holds a strong allure.
Detours and Lessons
I've been taking detours off of Highway 40 to ride along sections of the old Route 66 for over 20 years. Each time, it feels different. It’s like the past is rising through my tires, calling me to learn more. So when I finally got the chance to drive the entire route, I didn’t hesitate.
I didn't know much about its history beyond that it was a cool-sounding road—a place where people went to get their kicks. To me, it was about rock and roll and classic cars. It was a chance to drive a legendary road and see giant balls of twine. Later, I learned that Cawker City's Largest Ball of Twine was a detour more than five hours north of Route 66. So, I decided instead to track down as many "Muffler Men" as I could find along the way, closer to the route. I was happy to be among the ghosts of cars that once cruised this great highway, like the ones that often only appear on Fridays to be admired alongside burger stands.
As the journey went on and mile markers passed, it proved to be more challenging than I had expected. Breakdowns of all kinds plagued the trip; mine, my co-pilot Mark's, and the car’s mechanical issues nearly wrecked me. But it also reminded me of my privilege. I was out there, after all, and it was my choice. So I’ll try to tone down any whining.
I learned lessons from those who fell for hard promises, those who traveled the road, trading green pastures for dreams of bountiful orchards, and those who set up along the way to make and, in many cases, lose their fortunes.
Reflecting on the Drive
As I go through over 2,000 trip photographs, I often find myself with more questions than answers—many of the pictures raise more questions than they resolve. But memories of good times flood back as well. The little things, like neon lights, chicken-fried steak—especially chicken-fried steak—and the thrill of uncovering bits of long-forgotten history.
Route 66 is the quintessential place to chase dreams, with fellow Highway Companions all in pursuit of the sights, sounds, and tastes of the Great American Road Trip. It remains, for those who believe that windows should be rolled down and radios turned up loud. Little runways of a sort, if only temporarily, who trust that there's something good waiting just down the road of life, and that the history and lessons of Route 66 might show us just a little bit of the mystery within ourselves and each other.
What follows is my story about what I learned on Route 66, regarding the road, relationships, and myself. Like any good road trip, there will be detours.
I’d be remiss if I didn't mention my love for music, books, and movies, which will undoubtedly influence these pages. For any Tom Petty fans, please forgive the shameless lyrical references so far.
In what you are about to read, I’ve done my best to stick to the facts, but in the spirit of Mark Twain, who said, "Never let the truth get in the way of a good story," some parts may include some creative license. The remarkable thing is that the “true stuff” is likely to sound the most fabricated.