Our obsession with Route 66 started innocently enough (as perhaps most obsessions do). Faced with the necessity of driving cross-country, Ed, my partner and photographer (and significant other), suggested “Why not drive Route 66.” In a world of fast food and fast highways, in which the goal is the destination, the idea of making a journey part of the pleasure was irresistible. Armed with books, maps, and an ever-filled cooler, we set out to find and drive the Main Street of America.

The Highway Hop -- Solution to a tricky drive

And immediately discovered that following the Mother Road is tricky, what with the dead ends, dirt roads, and multiple roads all claiming to be Route 66. Towns often did “alignments,” literally moving Route 66 from one road to another. It was easy when all they had to do was put up a sign marking another stretch of road the current Route 66.

We backed up, turned around, and sometimes cursed roads that simply ended. We soon learned to do the “highway hop” shuttling between sections of interstate highways and paved sections of Route 66, investigating the venerable and endangered highway heritage attractions along the way.

Illinois

Route 66 starts in Chicago, working its way towards the Pacific Ocean. Although Chicago does not lack history, much of that asphalt heritage is gone. But in Joliet we found the totally deliciously over-the-top Rialto Square Theatre with impossibly high ceilings carved and gilded and huge mirrored walls. It’s actually a restored “vaudeville movie palace” which opened in 1926. Today, you can still see shows as well as take a free tour into the history of the building. We were also treated to a brief demonstration of their prized1926 pipe organ, still belting out music. After the official tour was over, one of the guards motioned to us – go backstage and see the “graffiti” left by previous performers, everything from Care Bears Live to Alice Cooper.

Driving along the hushed streets of Odell, a town of just over 1000 people, it’s hard to imagine it was once so busy that the town actually constructed an underpass so the children could safely navigate to their public school across the road. We stood in the center of Route 66, looking left and right, with nary a car in sight.

Route 66 afficionados visit for a chance to see Odell’s Service Station on West Street. Opened in 1932 as a Standard Oil gas station has been lovingly restored by volunteers. It’s cheery white and blue paint, with its tiny house and canopy design charmed us. Set at the edge of this quiet town, it also makes a lovely picnic spot.

Although Route 66 fans know Mt. Olive because of the Soulsby family and their restored Shell gas station, truly another 1920s jewel, tiny Mt. Olive has a union history as well. Wandering along the roads, trying to stay on the ofttimes elusive Route 66, we found the Union Miner Cemetery and discovered that Mt. Olive is also the final resting place of Mother Jones, union organizer and general troublemaker in the best sense of the word. Arrested in 1902 for ignoring an injunction banning meetings by striking miners, Reese Blizzard, a West Virginia District Attorney, called her "the most dangerous woman in America."

Missouri

Like Chicago, St. Louis has much history, and many wonderful sights, but as we rolled through we had just one thought in mind – Ted Drewes. Or rather, Ted Drewes Frozen Custard, located on what was once Route 66. The custard comes in one flavor – vanilla. Period. But they do have toppings, and if you insist you can have a concrete – the delectable vanilla custard mixed with other flavors. But why mess with perfection? Get the vanilla and add a topping for a bit of diversity.

Cuba is another small town bypassed by the passing of the Main Street but as we wandered about looking for the painted walls earned Cuba the appellation of Route 66 Mural City, we met Peggy. One of the forces behind the wall mural project, she recognized us immediately as tourists and eager to share the history of the city, she pointed us towards the 12 outdoor murals on business walls along historic Route 66. The murals depict universal themes from the city’s history. In homage to Route 66, include three panels on the side of one of the historic Route 66 Phillips Petroleum Gas Stations.

Rolla (pronounced RAH-lla) is named after the North Carolina capital city Raleigh – with a slight southern drawl. The story goes that the name came from the new settlers, originally from North Carolina, who missed their hometown. We found the Totem Pole Trading Post still functioning as a gas station with the oldest working pumps in Missouri, and with the addition of a charming touristy gift shop filled with road memorabilia.

But we were really on the quest for the Cherokee Trail of Tears memorial. Route 66 between Rolla and Springfield overlays part of the infamous Trail of Tears, one of the shameful events of American history. In 1838 about 100,000 native Americans were forcibly removed from their homes in what is now the eastern United States to what was then called Indian Territory. Included were members of the Cherokee, Choctaw, Chickasaw, Creek, and Seminole nations. Although devastating for all, the Cherokee traveled over a thousand miles and many died along the way.

Larry Baggett had constructed a memorial to the Cherokee. Drawn to the history of the Trail of Tears, the story behind the memorial was more than enough to convince us to visit. Baggett bought the land with the goal of setting up a campground as a source of income. But after building his home there, he was visited by nightly knockings on his door, the manifestations of an old Cherokee who told him that spirits were still walking that trail. Abandoning his plans for the campground, Baggett instead created a commemoration of stone-and-concrete archways and sculptures.

Although the guidebooks showed pictures of vibrant works of folk art, lack of maintenance, time and care has caused serious erosion. The driveway was closed off, but it was still possible to see that the this thoughtful memorial was sadly dying of neglect.

Many of the small towns we passed didn’t survive the closing of the Main Street of America, and the rise of the superhighway. The remains of these towns, both those that have faded away, and those in the process of fading were scattered along the road. Route 66 between Halltown and Carthage the town of Rescue, Plew, and others – dilapidated stores, skeletons of motels, arrows pointing to restaurants now gone.