Curbside Roadtrip: The Cars of Route 66 – Tri-Fives, Movie Inspirations, a Converted School Bus, and Everyday Curbside Classics


My sons and I made a trip along old Route 66 over spring break, driving it across Illinois, Missouri and Oklahoma. I expected to find plenty of curbside classics along the Mother Road, and I was not disappointed. I photographed as many as I could. Here they are, from east to west.

Bob Waldmire was one of the best friends an old road ever had. Splitting his time between Arizona and Illinois, he traveled the Mother Road constantly, advocated for its preservation and was known for his road-related art. His home base was Springfield, Illinois, where he lived in this converted 1966 Cheverolet/Superior school bus. Waldmire died in 2009, and his bus is now parked outside the Route 66 Museum, in Pontiac, Illinois.


Waldmire traveled the road in this 1972 VW Bus, which is now on display inside the museum. This bus inspired the Fillmore character in the Pixar movie Cars.


This ’51 Chevy truck is parked in front of a garage in Carlinville, Illinois.


Even though this truck has all its fenders, a pair of rear fenders filled the bed.


Many of the old cars along the route advertised the route’s businesses; this one advertises for a Subway in Edwardsville, Illinois. I hope, however, that the logo peels off this ’56 Chevy’s flank easily.


Tri-fives were well represented on Route 66, and this was by far the nicest example I saw. Nostalgia for the road seems to be centered around the 1950s, but in reality, that’s when Route 66’s decline began as the Interstates began to replace it. The road’s greatest historical significance comes from its early days, the late 1920s and 1930s, when it provided a vital path across the southwest.


Old trucks were also well represented along the Mother Road. This ’62 Ford looks like a survivor.


Now that, my friends, is what a well-used truck bed is supposed to look like.


This 1950 Chevy is permanently parked over the grease pit of a former Standard station in Cuba, Missouri. Built in the 1930s, the station has always fronted the cabins of the Wagon Wheel Motel. You can see some of the cabins behind the Chevy. The entire site was renovated a few years ago. We stayed overnight, and it was a highlight of our trip.


This mid-1980s Nissan truck was parked in a church lot in Cuba. I’ve never seen a flatbed Nissan before!


This 1951 International Harvester tow truck inspired the Tow Mater character in the movie Cars. It’s now rusting away along the route, in Galena, Kansas.


This 1966 Olds F-85 was parked just down the road in Galena, in front of the store it advertises. I can’t remember the last time I saw an F-85! Candy and jerky are certainly not an obvious pairing, but my sons and I stepped inside to sample both, and somehow it works. I especially liked the jerky, and bought a ton of it for us to snack on during the rest of the trip.


This 1970 Ford Mustang convertible was parked in front of a restaurant in Vinita, Oklahoma–and it’s for sale!


Route 66 no longer appears on maps, and in many places the Interstates have messed up its routing. In order to help me find the old road, I bought the book EZ66 Guide for Travelers, by Jerry McClanahan, an author and artist best known for his works about Route 66. His indispensable book shows maps of the route and tells you where to turn. When we reached the page for Chandler, Oklahoma, Jerry not only called it out as the town in which he lived, but actually gave his home phone number and invited visitors! When I called him at home, he invited us to stop by his home and art gallery, where he’s slowly restoring this ’57 Chevy wagon.

Jerry’s paintings of scenes along the route routinely feature old cars, mostly 1950s classics. Jerry said that people from all over the world come to the United States to drive Route 66, and those who visit his studio are most excited about the paintings that feature cars from that era. I was most drawn to his painting of a 1930s service station (it’s still standing along the route, in Illinois) with a 1948 Tucker parked out front.

I have to think that people looking for 1950s America along the Mother Road will be disappointed. Long stretches of the old highway parallel various Interstates and frankly, those segments aren’t very interesting. Also, towns along the route suffered economically when the Interstate took all the traffic away, and many of them show decades of decline.

Still, preservationists and businesspeople along the route keep it alive, and enough of them to provide good things to see and do still dot the road. They made it a good trip for us.