Part 1: Historic Route 66 Begins
There's a road that stretches across the Heart of America, a thread of pavement and promise that has captured the imaginations of travelers for nearly a century. For Caleb, Florian, and me, it was a road we'd always dreamed of riding in its entirety—all 2,448 miles of Route 66 connecting Chicago, IL, so Santa Monica, CA.
The idea of completing Route 66 was more than just ticking off a bucket list item. It was our chance to live the iconic dream of the Great American Road Trip, to feel the pulse of history beneath our wheels, and to embrace the sense of freedom that only the open road (and a Harley-Davidson motorcycle) can provide. There’s a certain magic to this historic highway, a mystique that whispers of adventure and countless stories etched into its asphalt. Route 66 was calling—and we answered.
It was already sweltering as we stepped out of Lou Michell’s restaurant onto the streets of Chicago. Our bellies had been filled at one of the oldest restaurants in town, having served hearty breakfasts to travelers since the early 1920s. For most people who make the Route 66 pilgrimage, this is the place to start—including Christa and Christian Neuhauser, who started their tour 30 years ago. After recreating a timeless snapshot of our bikes parked in front of the restaurant, we hit the road.
The streets of the Windy City were busy, and not the ideal place for three Harley-Davidson baggers, especially when it was already 95 degrees at 8 a.m. We weren’t made for city life, and our first priority was to get the heck out of Dodge. Or, well, Chicago.
Motorcycles & Gear
2024 Harley-Davidson Road Glides and Street Glide
Helmet: HJC RPHA 11 Pro, Arai Signet Q
Pants: Klim Outrider Pants, Klim K Forty 3 Riding Jeans
Jacket: Klim Induction, Klim Marrakesh, REV’IT! Overshirt Tracer Air 2
Boots: Klim Black Jak, Danner Logger, TCX Hero 2 WP
Gloves: Klim Dakar, Alpinestars
Luggage: Peak Design 45L Travel Backpack, Peak Design 30L Travel Backpack
Comm System: Cardo Packtalk Edge (x7)
Camera: Nikon Z6II, 24-70mm F2.8, 28-300 F3.5
As we navigated the busy streets, I was filled with nervous excitement for what the next 17 days had in store for us. What would we find along this route? How many untold stories lay between the layers of pavement that have been spread over the last 100 years? Would Caleb and Florian get tired of chatting with me in the helmets? We were about to find out.
Establishing Route 66
In 1926, Route 66 was established as one of the original highways in the U.S. Highway System. Commissioner Cyrus Avery led the efforts to connect Chicago to Santa Monica by way of his hometown, Tulsa, OK. While the roads already existed for the most part, Avery’s plan was to map a designated route and have it paved—the end goal being to make transportation across our country both easier and faster.
The economic hardships of the Great Depression drove many families to travel Route 66 in search of work and a better life during the 1930s. This was particularly true for farmers and laborers escaping the Dust Bowl—a devastating series of droughts and dust storms that ravaged states like Oklahoma, Texas, Kansas, and Arkansas. Many headed west to California, which was seen as a land of opportunity with fertile farmland. People traversing the route were truly chasing the American Dream.