Getting Kicked by a Route 66 Road Trip

A vintage car enthusiast sets out for a bucket list Route 66 road trip only to find that it doesn’t quite live up to the hype. Here’s his story of getting kicked by Route 66.

In an age of interstate superhighways, it’s hard to believe that Route 66 used to be such a major thoroughfare. The two-lane roadway seems impossibly narrow. Fortunately, we passed few other cars as we rolled along in our wide SUV.

It was my wife’s idea to drive from Chicago to central Illinois via the Mother Road. I had just finished rebuilding a 1967 Cobra Jet Mustang and it seemed somehow fitting that we should take the low road in honor of the heyday of American road trips. (We didn’t drive the Mustang–it’s not quite ready for a road trip. Next time.)

Realities of a Route 66 Road Trip

We chose to skip the portion of Route 66 that runs through Chicago. We’ve driven it many times and we were anxious to get started on our trip. Turns out we shouldn’t have been in such a rush.

We took the Interstate to Braidwood, about an hour southwest of Chicago, where we jumped off the super highway and hit the super slow way.

Reliving the 1950s on a Route 66 Road Trip

First stop: a Route 66 milkshake from the Polka Dot Drive-In. It was a good choice. The milkshake and chocolate malt were officially rich and headache-inducing while the décor was all 1950s. Elvis Presley and Marilyn Monroe adorned the walls everywhere, including the bathrooms where Marilyn kept watch as I peed. Elvis kept my wife company in the women’s bathroom.

Then it was back on Route 66, where we drove. And drove. And stopped. Then turned. And looked for the next directional signpost.

And pretty quickly got tired of the whole thing.

Finding Our Way on Route 66

The state has done a good job of marking the route with Route 66 signs and some painstakingly researched directions we downloaded from the Internet helped us find our way. But the few times we ventured off the Mother Road we found it difficult to find our way back.

We drove through a few one-stoplight towns and there were a few signature Route 66 touches along the way.

We found the gigantic Paul Bunyan statue holding a hot dog that had once stood alongside Route 66 in Berwyn. In that Chicago suburb, the road is named Ogden Avenue and is a busy but usually effective alternative way into and out of the city during rush hours. The statue was relocated years ago to Atlanta, Illinois, where he still holds the hot dog and stands next to a sign explaining his history.

On the road into Pontiac, we found the BurmaShave words of wisdom: “Why is it when you try to pass, the guy in front gets twice as fast?” And, “If hugging is your sport, trade in your car for a davenport.” (My wife had to explain that a “davenport” is what they used to call a couch.)

The Right Car for a Route 66 Road Trip

Sadly, our Route 66 road trip was more boring than thrilling. For most of the way, the road lay between a set of railroad tracks and Interstate 55, the superhighway that made Route 66 obsolete. At a few points along the way, another narrower asphalt path, overgrown with weeds, ran alongside our Route 66. It was, we believe, the original Route 66.