The Road That Gave It Back

On September 4, 2014, my friend Jen Dragon and I set out from Chicago on an epic journey across the United States, joining eighty riders for the annual Ride for the Relay along the legendary Route 66. Founded in 2006, the rally is equal parts adventure and devotion: a cross-country pilgrimage along the Great Mother Road to raise funds for the American Cancer Society. Of the eighty participants, nearly all rode motorcycles. Jen and I were one of only two cars in the rally, shuttling a flame-decaled 2001 Toyota across the country for a friend—hardly a Thelma and Louise Thunderbird, but sturdy and willing.

We gathered in Chicago near the elusive beginning of Route 66 beside Lake Michigan. Years earlier, my husband Richard and I had driven in circles searching for the official plaque. This time, I would find it, and photograph it, before we rolled west. Riders had come from eighteen states, most between the ages of fifty and seventy, men and women alike, many women riding their own bikes. Each morning began with a blessing of the road and a dedication to someone lost to or living with cancer. It was reverent, moving, and deeply human.

I dedicated my ride to our dear friend Claudia Ainsley, “Bubby”, whose legendary baked goods once filled our Kingston café, Bistro-to-Go, with warmth and joy. Her illness came swiftly and cruelly. When I first committed to this fundraising journey, I had no idea it would become a tribute to her. Now it felt essential. Claudia rode with me in spirit, mile after mile.

My love of the great American roadside began long before this trip. As a child, I spent summers on family road trips, staying at motels and eating at Mom ’n Pop restaurants across the country. Even then, I documented what I loved, saving souvenirs, creating scrapbooks, and keeping diaries that I still have today. By the 1970s, I began to notice that many of the signs, buildings, and businesses that had once defined the roadside landscape were slowly disappearing.

Wherever I traveled, I photographed, and often painted, these fading icons. Without quite realizing it, I was becoming an amateur preservationist. I also began collecting and writing the stories of these businesses, eventually sharing them through my blog. Many of these stories, along with my paintings and photographs of America’s roadside icons, can be found on my website.

After decades of watching this visual history erode, Route 66 stood apart. Here, preservation is intentional. Neon is relit. Motels are restored. Diners reopen. The Mother Road is not merely remembered, it is actively loved. That distinction matters profoundly to me as an artist. This road is a living archive, sustained by people who believe memory has value.

Day after day, as the landscape unfolded, we reveled in the wealth of roadside attractions: in Illinois, the Gemini Giant and Henry’s Hot Dogs; in Missouri, the giant catsup bottle, the Boots Motel, and the Wagon Wheel Motel. In Oklahoma, we met Dawn Welch at the Rock Café, the original inspiration for the Disney movie Cars. In Amarillo, Texas, we dined at one of the most entertaining spots on earth, the Big Texan Steak Ranch, and marveled at Cadillac Ranch. New Mexico delighted us at every turn, beginning with Tucumcari, home to the Blue Swallow Motel and a host of other incredible neon signs. Nearby Santa Rosa yielded three of my favorite Route 66 paintings: La Mesa Motel, Tower Motel, and Comet II Drive-In. In Arizona, we were “standin’ on a corner,” enchanted by the Wigwam Motel and the Jack Rabbit Trading Post, and awed by the Grand Canyon and the Painted Desert. Finally, we reached California and our journey’s culmination at the Santa Monica Pier.

I documented obsessively, three cameras, nightly journaling, knowing these images would later become paintings. Neon signs glowed at dusk. Abandoned motels whispered stories. On this road, the visual language I had been chasing for years revealed itself fully.

Then the unthinkable happened. At the Grand Canyon, my journal and iPad were stolen from the trunk of our car. I was devastated. The loss felt like the erasure of the journey itself, the death of a carefully imagined record I had planned for months.

But the road kept going, and so did we. Kindness appeared. The riders became family. By the time we reached Santa Monica, grief and gratitude had merged together. Route 66 does that, it invites reflection, connection, and a longing that doesn’t fade once the journey ends.

And then, after I returned home, a miracle occurred. A woman in Arizona contacted me, saying she might have found something of mine and asked if I could answer a few questions. I did, heart pounding. She lived in a small desert town near the Grand Canyon and had found my journal and my iPad lying together in a ditch by the side of the road. Hallelujah. My precious record of the journey was returned to me, intact.

Route 66 gives back what it takes. As an artist, as a traveler, as a human being, I believe that now more than ever. This road doesn’t just preserve history, it reminds us why preserving it matters. And once you travel it, part of you will always want to return.