From June 6th to June 20th, I helped lead the Main Street of America Route 66 Centennial Caravan. It was exhausting, exciting, devastating, and rewarding. Overall, it exceeded my expectations, though that came with a high cost. It was the first time I had traveled Route 66 from end-to-end in a single trip. For the next few weeks, I will be writing in detail about our journey across the country and you will hopefully understand why I chose all of those words. But first, I need to write about how it all came about.
Conversations about organizing a Centennial Caravan began in mid-2024. As the head of the State Advocacy Working Group with the Route 66 Road Ahead Partnership, that gave me a monthly touch-point with other statewide Route 66 organizations. Even though the centennial year was still a ways off, I brought up the fact that an organized trip along the entire corridor would be a great way to celebrate the road’s 100th Anniversary. That idea quickly found traction and, as often happens in such situations, came back to me with the direction that I be in charge of its execution.
Unlike some of my peers in the other Route 66 states, I had never organized any kind of motor tour or cruise. This was going to be new territory for me.
I reached out to a few of them to get an idea of how they organized their motor tours, usually one-or-two-days in length, and how they determined timing. I engaged my team at the National Trust for Historic Preservation to get their input. I wondered how we were going to PAY for something of this magnitude. All of that would come in time – the first thing I needed to do was start getting the word out. So I called Nancy Barlow.
I’ve known Nancy for years. I met her and her husband, K.C., at my first Birthplace of Route 66 Festival in Springfield, Missouri about a decade ago. I bump into them on the road every so often (usually in Tucumcari, NM) and they are big supporters of small businesses on the route. Nancy also has her own advertising firm. I asked if she would design a logo and general branding for the Caravan and she agreed. What resulted from that was the green triangular logo that honored the road and set us apart from other efforts to mark the road’s big anniversary.
With the logo in hand, I built a website. I engaged my peers from across the Route 66 network from Illinois to California to help flesh out each day’s schedule. It was Scott Piotrowski, President of the California Historic Route 66 Association at the time, that recommended we go west-to-east rather than the so-called traditional direction from Chicago to Santa Monica. It would set us apart from any other cruises that came together, it would allow us to encounter more travelers organically, and it would give California a chance to shine rather than be relegated to a get-to-the-ocean-as-fast-as-you-can leg of the journey. It all made perfect sense, and so it was decided. We selected a start date of 6/6 (which, also, just made sense) and started building a three week itinerary.
In March of 2025, the Road Ahead had their annual board meeting in Albuquerque. On the way home to Tulsa, Samantha and I stopped at the Big Texan where we had breakfast with owner Bobby Lee. During our conversation, I mentioned that we were in the early stages of putting together an end-to-end cruise for the Centennial. Immediately, he said he would be interested in joining and hosting a 72 oz. Steak Challenge every night along the way. It was an incredible idea – and it was his instant interest that really lit the fire under me to get serious about making it happen.
Our Working Group decided that the caravan would focus on preservation and revitalization, which are core parts of our collective missions. Route 66 turning 100 was a great time to celebrate the road’s history, but it was also a great time to show that the road was very much alive. New stories were being added to its mileage every day. Of course, our scheduled stops wouldn’t be totally exclusive to this focus, but it would help us whittle it down a bit.
The biggest hurdle we had was funding. Three weeks on the road for more than a dozen vehicles isn’t cheap and none of our respective organizations had deep pockets. We were all non-profits and most of us were 100% volunteer operated. We anticipated having some funding available through Road Ahead centennial fundraising efforts, but we needed to stretch every dollar. Both the Oklahoma Route 66 Association and the Illinois Route 66 Scenic Byway had good working relationships with Best Western Hotels and the company had a presence along the entire route, so we reached out to them to see if they would be interested in working with us on this ambitious project. I am so incredibly thankful that they said yes! Not only did they cover rooms for our leadership team throughout the entire journey, but they offered affiliate links for others to use that would raise a little money for the Road Ahead’s Preservation and Economic Development Grant. They also provided giveaway keychains and a few locations to hold the Big Texan’s steak challenge. Stuckey’s came on board, too, as did Route 66 Navigation.
Now we needed to identify who would actually be traveling on this trip. I never considered not being involved every single day – so Oklahoma was covered. Each state organization was tasked with selecting someone to represent them for the duration of the Caravan and arranging a vehicle to carry them along the way. We made space for a National Car and an International Car, each represented by members of the Road Ahead’s working groups. Dean Kennedy, our Roadie Representative in the National Car, recommended a photographer out of Albuquerque named Jessica Roybal (and after our first meeting, it was clear she was the absolute right choice.) The National Trust for Historic Preservation’s GIS Team came on board with a project to photograph and map the entire route. The Big Texan was true to their word, committing to nearly two dozen steak challenges and bringing along a special media team called GoRoute66.com to handle storytelling and streaming broadcasts of each day’s activities. They were even bringing Big Moo, their giant cow! Overall, it was a motley but dedicated crew.
We had one more question we needed to answer. How do we involve the public? The structure of the caravan had already morphed from a singular focus of preservation and non-profit leadership into something broader…and what better way to show the vitality of the Route 66 corridor than invite the public to tag along? I set up a simple form on the website clearly stating that anyone that wanted to join was welcome to for as long or as little as they’d like, but that they were basically on their own for the trip. There would be no way that I or the other leaders could provide the direction and heavy engagement that is required on a full-fledged motor tour for the entire three weeks.
Slowly, through 2025 and early 2026, these pieces went into place. Official participants were selected, the itinerary was finalized, press releases went out. We reached out to communities, attractions, and businesses to let them know we were coming. More than 350 people signed up to join us along the way. Before I knew it, it was time to get to Santa Monica to kick the whole thing off. Speaking of kickoff…
One more piece had fallen into place for the start of this incredible journey. In 2024, I had toured the Will Rogers State Historic Park in the Palisades and met people deeply committed to keeping Will’s legacy alive. I’d already known Jennifer Rogers, Will’s great-grandaughter, for a few years, but this was an introduction into a larger world. Even then, Larry Nemecek (President of Will Rogers Ranch Foundation) said they were planning on tying the Centennial into their work – after all, Route 66 was also known as the Will Rogers Highway. It was a great idea. Tragically, in January of 2025, the Palisades Fire destroyed Will’s home and his stable. The future was uncertain…but, if anything, I felt that this strengthened our need to highlight the park in some way.
In early 2026, I reached out to the Will Rogers Ranch Foundation and asked if they would be interested in hosting a kickoff event the evening before our departure. I told them that I wanted people to know that the Will Rogers story was still important and that even though the structures were gone, the park still had story to tell. Will’s legacy was still alive. They were delighted – and they pulled out all the stops to organize a lovely evening in the park for our team and any caravaners that were starting the journey with us in Santa Monica. They even arranged to have some special classic cars come out, including a gorgeous vintage Highway Patrol car. Mel’s Diner, situated at the official endpoint of Route 66, catered the food. Since our group was too large to make that a stop on the way out of town, it was the perfect way to still engage them as a part of the journey. Check out the full photo spread here.
As the sun set on June 5th, 2026, we were all excited. I was also a bit nervous. How would the trip go? Were we truly prepared? What had we forgotten to plan for? What if someone got into an accident? How many people would show up each day? These questions and many more were all rushing through my mind. But sleep eventually came; the next morning, the daily pattern for the next three weeks emerged. More than two years of work had led up to that moment.
Over the next few weeks, I’ll be posting details about the journey: the sights we saw, the people we met, the trials we faced. There was tragedy. There was jubilation. The full gamut of human emotion made an appearance between California and Illinois. At the center of it all was a highway that has connected this country for a century: Route 66.
Rhys' Pieces 