At quirky roadside attractions like the 1960s Motel Shawford and Restaurant in Santa Rosa, New Mexico, Route 66 travelers can get a colorful impression of America. Photo by Thomas Hawk

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In the 1940s, everyone was humming about how to “get your kicks on Route 66,” thanks to Nat King Cole and his hit.

In the 1960s, the road fed the fevered imagination of an entire generation due to the two cool, good-looking guys in their hot Corvette who starred in the TV show “Route 66” during those years.

Back in the day, yours truly — a decidedly uncool, homely teenager driving a vomit-green ‘54 Pontiac that seized up with vapor lock whenever it got hot — fantasized often about taking the classic American road trip down the storied route.

Finally, just this past summer, that teenager — now a cooler, better-looking geezer (whose delusions are fueled by age) — had an opportunity to fulfill that fantasy on a Route 66 road trip hosted by a company called Two Lane America.

For 12 days, my wife and I traveled in a caravan of six cars, including a vintage 1966 Corvette, from Chicago to the route’s terminus on Santa Monica Pier. Instead of driving our own car, as most participants do, my wife and I rode along with the owner of the company and his father in the lead van. We also got a lift from other drivers in the caravan to get their perspective on the trip and on America.

In his classic novel The Grapes of Wrath, John Steinbeck called Route 66 the Mother Road because it was an escape route for desperate migrants heading west in search of jobs and new lives. The Model T made it possible; the Depression made it necessary.

For Okies fleeing the Dust Bowl in the 1930s for the promised land of California, former soldiers heading west after the end of WWII, and beatniks and hippies searching for enlightenment, artistic freedom and a joint in the 50s and 60s — Route 66 has been a highway of hope for anyone pursuing a better life.

Ultimately, this trip gave me an appreciation for the American ethos. In many ways, Route 66 is symbolic of the American character — a metaphor for the magnetic pull of the frontier and the freedom and adventure of the open road.

And not just Americans get this. We ran into many foreign tourists, including a motorcycle club from Hong Kong and another from Germany making their thunderous way along the Mother Road.

More than just roadside kitsch

As we rolled down the highway day after day, layers of experience unfolded like the sedimentary strata of an archeological dig.

The top layer consisted of the kitschy, iconic sites we saw along the way: old diners, gas stations, motels, vintage cars, museums, architectural landmarks and collections of memorabilia.

We saw lots of oddities, roadside attractions and noteworthy sites, including Mickey Mantle’s childhood home, the Cadillac Ranch, the Blue Whale of Catoosa, and a huge statue of the Muffler Man, now holding a gigantic hot dog in place of the muffler.

Roadside Americana is just what you’d expect on Route 66, but we also saw another layer of the country during our journey — small-town middle America, Main Street USA, that vast land between the coasts that those of us who don’t live there sometimes condescendingly refer to as “flyover country.”

It was an eye opener. We visited places I would have otherwise overlooked that filled in the picture of what the U.S. is all about.

For almost two weeks I was immersed in the Heartland, passing through small towns with friendly people and stately houses flying large American flags, and eating huge portions of grits, biscuits with gravy and red meat in various forms.

It wasn’t all lighthearted fun and rose-colored nostalgia for a bygone era, though. We made at least one sobering stop along the way: the Oklahoma City Memorial for the 168 victims of the terrorist bombing of the Murrah Federal Building in 1995, including 19 young children.

The memorial is part of our American story, too. It was impossible to get through the museum with a dry eye, and I left with a sense of foreboding that this was probably not the last such memorial we will ever have to build.

A life-changing journey

On the ninth day of the trip, we visited the Mineshaft Tavern, the oldest bar in New Mexico, in the former ghost town and now booming tourist destination of Madrid, about 30 miles from Santa Fe.

As I sat at the bar, I recalled my own journey on the highway of dreams 44 years ago.

Most of my pilgrimage from Allentown, Pennsylvania to Venice, California was on Interstate I-40, not Route 66 (though the routes often overlapped), and I wasn’t fleeing the Dust Bowl. I was fleeing my own personal depression brought on by losing my job, my girlfriend and the publishing contract for my first book, all in the space of just a few months.

During that trip, I paused for two months to visit a friend in Santa Fe and help him fix up a dilapidated miner’s shack in Madrid. We usually ended our workdays at the bar in the Mineshaft. That was the summer my luck turned around.

Sitting at that same bar, I understood at a deep, personal level what Route 66 meant for the millions of seekers and dreamers who made their way west on that narrow, dusty road. I only hope that their dreams worked out as well as mine.

Two Lane America’s 13-day tours of Route 66 start at $2,399 per person. For more information, visit guidedroute66tours.com. More photos are on Don’s website, adventuretransformations.com.