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Drawn to the road
Robert "Bob" Waldmire was raised in Springfield, Illinois. The family owned the Cozy Dog Drive-In, which invented the corn dog and served them to Route 66 travelers.
But Bob was not interested in running the family business. He wanted to travel and sketch the world around him.
Norman Oklahoma Calendar Art (1976)Oklahoma Route 66 Association
Bob left Springfield after high school and traveled the country, stopping in college towns to sketch the area. He sold his art to stores and cities, moving on to the next town when he pleased.
Bob's work expanded from cities to states and entire regions. His maps not only featured landmarks and history, but flora and fauna of the area. He adopted a hippie lifestyle, became a vegetarian, and started working pro-environmental messages into his work.
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Discovering 66
In 1987, an interstate detour led him onto Historic Route 66 & he fell in love with the highway. "Back on 66, there was this bump-ba-bump-ba-bump as I drove over the poured concrete slabs - a feeling of being closer to the land and nature."
Bob began sketching places along Route 66, creating a sixteen-page map and legend in 1992. His passion also led him to purchase an old store and service station in Hackberry, Arizona, and convert it into a visitor's center.
Bob at Hackberry (1995) by Michael WallisOklahoma Route 66 Association
International Bioregional Route 66 Visitor's Center
Bob reopened the old store, living out of a converted school bus and welcoming visitors from around the world. But his wanderlust did not go away; after six years, he sold the property and made a new plan.
Bob Waldmire in Portal by Johnnie MeierOklahoma Route 66 Association
After Hackberry, Bob moved to Portal, Arizona, and lived off the land in the Chiricahua Mountains. He split his time between his homestead and the open road, where he continued to create art and connect with the 'linear community' of Route 66.
Bob's connection to the Route 66 community only strengthened; other travelers have many stories of encountering Bob on the road, perhaps sketching in a late-night Denny's or saving a critter from getting run over.
Author and historian Michael Wallis remembers encountering Bob in the ghost town of Glenrio, which straddles the Texas and New Mexico border.
Bob's Blue Ribbon Award (2000) by Bob WaldmireOklahoma Route 66 Association
Bob had a certificate he would hand out to restaurants he encountered that had an excellent salad bar.
Waldmire Fillmore (2006) by Bob WaldmireOklahoma Route 66 Association
A principled vegetarian
Bob was so well-known along the road that Pixar Animation Studios wanted to name their Volkswagen character in their movie Cars after him. But he didn't want his name associated with fast food outside of his culinary lifestyle. Instead, Disney named their minibus Fillmore.
Bob's Last Art Show (2009) by Johnnie MeierOklahoma Route 66 Association
In October of 2009, Bob announced he had cancer. He'd known for some time, but chose to live on his own terms. A month later, Bob had his Last Art Show at the family restaurant in Springfield, IL. People came from all over the world to pay their respects. Bob passed in December.
Waldmire Mural in Pontiac (2025-08-11) by Rhys MartinOklahoma Route 66 Association
Not forgotten
Bob may be gone, but his art lives on. His legend continues to grow more than a decade after his death. New people come to Route 66 every day, pick up a postcard, and learn a little about the highway, its natural environment, and a man that made the road his home.
At the end of his letters, Bob would close with a short, simple phrase: For the Earth.
Many thanks to Buz and the rest of the Waldmire family for their support!
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