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A Road Trip Down Route 66 Is Corny, But It's Also Necessary

Illustration: Elena Scotti (Photos: Benjamin Preston/Jalopnik, Getty Images)
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It’s a fading, crumbling snapshot of America as aspiring industrial superpower and as self-contained promised land. It’s part self-promotion, part nostalgia and all variety of landmarks, roadside attractions and stunning natural scenery. The sum of all its parts is a story—a story about leisure, escape, progress, decline. As it stands Route 66 is, in its way, the story of America.

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Photo: Benjamin Preston

(Full Disclosure: Chevrolet was keen to show off its last front-engined Corvette, and let me borrow one for a week. Chevy was happy to lend me one of its cars for this trip. A previous drive of mine, nine days of life along the border, didn’t get an enthusiastic reception from GM, or any other carmaker for that matter.) 

A cool breeze blew across the waters of Lake Michigan as I regarded its profound blueness from the chunky gray blocks that form Queen’s Landing in Chicago. An Elkhart Lake Blue 2019 Corvette Grand Sport was parked nearby and the weather was early summer at its best.

It was a perfect day to begin a week-long, often roofless trip along historic Route 66, which begins on E Jackson Drive at Chicago’s lakefront and stretches more than 2,400 miles to Santa Monica, California, on the Pacific Coast.

Image for article titled A Road Trip Down Route 66 Is Corny, But It's Also Necessary
Photo: Benjamin Preston

To best explain Route 66, it’s best that I begin at the end. By that I mean the end of its days as an official numbered route in the US highway system.

Route 66, which had been established in 1926 from a mish-mash of fragments of other highways, was decommissioned in 1985, the year after the final stretch of Interstate 40 replaced its last remaining commissioned chunk in Williams, Arizona.

What’s left today is a collection of state and local highways, interstate access roads and—in some cases—cracked, weed-eaten pavement. In some places, superhighway construction completely obliterated long stretches of 66 where the original road bed was used to support a modern, limited-access freeway in the decades following the federal legislation that established the interstate highway system.

But the memories are still there, emblazoned upon the American cultural landscape by John Steinbeck’s novel The Grapes of Wrath, Nat King Cole’s recording of “(Get Your Kicks On) Route 66,” Jack Kerouac’s novel On the Road, the 1960s television series “Route 66" and, of course, the Pixar film series “Cars.” No other road has claimed so large a share of the national consciousness as the highway Steinbeck called The Mother Road.

Still, in modern times, it can be a bit difficult to follow the the physical route. For starters, it ran along different alignments over the years. In the early days, Route 66 went through every city, town and hamlet it crossed. Then in the late ’30s, bypasses were added to ease congestion. In some cases, the number was assigned to a completely different path, as happened when highway officials shortened the route between Santa Rosa, New Mexico and Albuquerque by cutting off the loop running northward through Santa Fe. More direct alignments gradually took precedence over earlier meanders, leaving mountain villages like Oatman, Arizona in the lurch.

As these changes occurred over the decades, roadside attractions that had been created to lure travelers and their dollars briefly away from the steady hum of forward progress gradually dried up and went away. But not all of them. Today, there remains a long string of them—some very old and some introduced in modern times, both to help reinstall the road in our consciousness and to take advantage of that realization.

In many cases—as with the novel Round Barn in Arcadia, Oklahoma—these disparate efforts manifested as local communities banding together to save famous, but nearly forgotten landmarks from the ravages of time. In other cases—a Magnolia gas station in Shamrock, Texas and the long-abandoned Blue Swallow Motel in Tucumcari, New Mexico, for example—someone just decided to do something about bringing deterioration to a halt. Either way, the deep-rooted power of nostalgia had something to do with it, but so did the need to protect a relatively young national culture from disappearing. That culture tends to be commercial, but attracting customers has brought forth some of the richest creativity the world has ever seen. So it’s no surprise that people have stepped outside their comfort zones to save aging roadside attractions.

Like any modern-day Route 66 traveler, I did the best I could to follow what was left of the road, making executive decisions as I went regarding which alignment I would follow at any given time. I picked up a copy of Drew Knowles’ Route 66 Adventure Handbook, as well as Jim Ross and Jerry McClanahan’s Here It Is! Route 66 Map Series. Both were extremely helpful, and pointed out scores of attractions I may never have found otherwise. In most cases, I stopped at the places that looked most interesting, but I often had to pick the fastest route (or take the interstate) in the overarching interest of reaching California in a week’s time. As a pair of French tourists I ran into at several points of interest in Missouri pointed out, a week isn’t a lot of time to explore the myriad curiosities along 2,400 miles of American history.

“Don’t worry,” I said, flashing them a grin. “I’m driving a really fast car.”

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Photo: Benjamin Preston

In Chicago—as in other large-ish cities along Route 66, like St. Louis, Tulsa and Albuquerque—66 is just another road. The brown and white signs denoting it as a historic route are about all that differentiates it from the multidecadal patchwork of urban development that forms the backdrop of any city. The highway didn’t really start feeling like something out of yesteryear until I was miles away from the Windy City, cruising through farmland with the Corvette’s targa top open. In much of Illinois, the parts of 66 that haven’t been subsumed by I-55 are still extant as a median-divided four-lane highway, although two of the lanes repose in weed-choked dereliction.

At this point, you may wonder why I chose to travel Route 66 from east to west. It’s simple: Manifest Destiny. It’s a complicated American cultural legacy with a lot of heavy baggage associated with it, but as Route 66 has inculcated itself in modern culture, so the 19th century compunction to carve out (steal from Native Americans, mostly) new frontiers in a drive to spread European-derived civilization from the original Atlantic Coast settlements all the way to the Pacific Ocean has informed our collective “Go west, young man!” mentality.

Also, it’s really nice to end up on the California coast after driving through miles and miles of sweltering desert.

Other than that, there’s absolutely no reason why Route 66 can’t be driven the other way around. US expansion in the lower 48 is, after all, a done deal. (At least I hope so.)

Pontiac, Illinois is where I encountered the first of many murals I would see along the way. They were a perfect representation of what 66 is today: restored vintage ads, mostly for products that no longer exist, and richly painted portraits of an idealized, once-upon-a-time Route 66 existence. All that was sprinkled into the framework of a quiet, mostly empty little town. I also began to see a lot of half century-old cars parked strategically by the roadside. Some were in front of otherwise defunct used car lots (because who buys used cars without leaning on Internet sites like Craigslist, eBay and, others were rotting quietly in front of long-shuttered motels. Seeing these cars anywhere else is a treat because the sighting feels random. On Route 66, they seemed more like props.

Further south in Illinois, I observed two examples of something I would see a lot of over the next several days: giant sculptures that were originally built to promote some kind of product. First was the muffler man of Atlanta, Illinois. He now holds a hot dog, although the only thing to eat in that part of the state after 9pm was a Snickers bar purchased from a local gas station. I also saw the giant catsup bottle in Collinsville, Illinois, a decaying suburb just east of St. Louis. It’s actually a water tower tank, and the plant it’s attached to no longer produces catsup. But it has been restored, one of many examples of community involvement in preserving local heritage along 66.

Crossing the Mississippi River into St. Louis on the 90-year-old Chain of Rocks Bridge, I had to hop on the freeway again before picking up the trail anew just south of the I-44/I-55 interchange. If we look at 66 in terms of modern freeways, it roughly follows the I-55 corridor from Chicago to St. Louis, then switches to the I-44 corridor across Missouri. In Oklahoma City, it shifts to the I-40 corridor, where it hovers for more than 1,200 miles until it hits Barstow, California. There, it follows the I-15 corridor in a southerly direction to San Bernardino, where it jogs due west near I-10 before fizzling out near the Santa Monica pier. So I was making the first major directional change along the route as I dove headlong into the wilds of Missouri.

If you ask most people who aren’t from Missouri what they know about it, they aren’t likely to have much to say. Or maybe they’ve seen The Outlaw Josey Wales and have some vague idea of its bloody history. In any event, Mark Twain’s home state is packed with fascinating historical and natural wonders. Route 66 cuts a nice swath right through the middle of all that, giving the curious traveler such gems as the Jesse James Wax Museum, or as I like to call it, the Jesse James Conspiracy Theory and Other Unrelated Old Stuff Museum. If its founder, Rudy Turilli, is to be believed, you may as well forget everything you know about Jesse James. With that said, it’s time for a bit of a sidetrack, something any good road trip should have.

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Photo: Benjamin Preston

Prevailing knowledge tells us that Jesse James was shot in the back by a member of his gang in St. Joseph, Missouri in 1882 and buried, dead, not long after. In 1948, Turilli—an Italian-American from New York City with a proclivity for shiny suits who had married into a family that owned a tourist attraction near Stanton, Missouri—produced a guy named J. Frank Dalton who claimed to be the real Jesse James. Dalton—er, James—didn’t die until 1951, and not until after Turilli and his father-in-law, Lester B. Dill, had thrown him a huge party to celebrate his 102nd birthday. Naturally, the festivities were held at Meramec Caverns, which Dill owned and operated. Today, the museum supports Turilli’s claim with a documentary film (produced by Turilli’s descendants), some dubious computer modeling printouts, a host of sagging wax statues and a plethora of unrelated (but labeled nonetheless) antique jetsam. At $9, the museum tour is definitely worthwhile.

The Jesse James story—along with Turilli’s version of it—is an interesting window into the American psyche. Here you have a guy who fought as a Confederate guerilla in a state deeply divided over the slavery issue. He went on to become a bandit the likes of which must have inspired all the famous motorized bank robbers who marauded the Midwest during the Great Depression (John Dillinger, Bonnie and Clyde, Baby Face Nelson and so on). This schism in Jamesian history—although, to be clear, I don’t think the Turilli school has many adherents—is a good example of the power of promotion. After all, what better way to bring in customers from a busy road than to stir up controversy, however minor?

There are lots of other things to see in Missouri, from curvy wooded roads through Ozark country to the restored Depression-era ghost town of Spencer, where you can still drive on the original Portland concrete slabs laid down in the 1920s. But one of the stops most worthy of your attention is Red Oak II, a place best described as a reconstituted hamlet. Tourbooks can only gloss over the substance of this place, but the owner of the Boots Court Motel in Carthage, Missouri—where Clark Gable is reported to have stayed a couple of times during the 1940s—sang its praises in such a way that I had no choice but to go.

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Photo: Benjamin Preston

A Carthaginian sculptor (not ancient Carthage, obviously) named Lowell Davis grew up in Red Oak, not far from Carthage. His grandfather owned the blacksmith shop, all his relatives lived there. After World War II, the place kind of dried up as people left for places with better job prospects. By the ‘70s, Davis was doing pretty well sculpting small figurines for companies that sold them to tourist shops and the like, and he began buying up buildings in his hometown. He had also bought a farm a few miles outside Carthage and had the buildings he’d purchased moved there. Thus was born Red Oak II, Davis’s version of his ancestral town. It has a diner, a church, some antique gas stations, a handful of rusty midcentury cars, and a bunch of his whimsical sculptures perched here and there for dramatic effect.

Davis was seated on his front porch, smoking a corncob pipe. He showed me his gallery and told me about his world travels and how he had moved Red Oak to its current location. Walking between the gallery and his house—which he said is a mishmash of Belle Starr’s childhood home and an old slave shack (a statement about the dichotomy of the American spirit, perhaps?)—Davis gestured toward an elaborately carved tombstone atop the cemetery hill he built from the spoils of the village pond. Most of the markers in the cemetery are duplicates of stones that have been replaced in local cemeteries over the years. He was able to get them for nothing from a monument company that had discarded them in its yard. But the stone presiding over the hill’s crown is different: It’s his.

“It’s waiting for me,” he said, raising an eyebrow as he shuffled back toward his porch chair.

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Photo: Benjamin Preston

Today’s interstate highway travelers would have little clue that 66 went through Kansas, because I-44 doesn’t. Route 66 covers less than 12 miles of Kansas, nipping a chunk off the state’s southeast corner before plunging into Oklahoma. Just as well. Kansas mining country is none too scenic. Also, there’s more to see in Oklahoma.

The Sooner State is widely considered to be the birthplace of 66 because it was Cyrus Avery’s base of operations. According to Oklahoma State University’s Cyrus S. Avery Collection, Avery was the man responsible for bringing the first paved Chicago-to-L.A. highway through Oklahoma rather than through Kansas, Colorado and Utah, as was originally planned. There’s little doubt that Avery’s work was aimed squarely at Oklahoma’s business community, which was always hungry for visitors’ dollars. But the people it helped most weren’t likely on the tycoon’s radar when he pushed for the southern alignment of 66.

Not long after the establishment of 66, the stock market crashed, plunging the country into the Great Depression. Avery’s highway became an escape route for millions of impoverished farmers as they fled the dust storms and economic privation of Oklahoma and Texas toward hoped-for jobs in the fields of California’s Central Valley. The Oklahoma Route 66 Museum, in Clinton, Oklahoma, features an exhibit filled with striking photographs of Okie migrants living in squalid camps as they struggled across the most inhospitable parts of the American continent in broken down old jalopies. That’s all ancient history by now, but bears a striking resemblance to the trials faced by impoverished migrants fleeing hunger and violence in the Northern Triangle countries of Central America today.

As I traveled west through Oklahoma, the climate became drier and towns further apart. Out-of-business motels that would have been used for truck parking further east assumed the character of ghost town buildings. Western Oklahoma and Eastern Texas are also where you’re most likely to find long stretches of old-fashioned concrete slab highway. Even though I-40 traffic roared past nearby along much of it, the pock-pock-hiss sound the slabs made beneath the car’s tires made it easy to conjure travel in the old days if I squinted my eyes and pretended I was driving something older. But it only worked if I slowed down and turned off the air conditioning.

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Photo: Benjamin Preston

The great American West is sky country. The clouds are fluffier and the horizon wider. Whether on an Indian reservation in New Mexico or an abandoned truck stop in Arizona, it’s the perfect, all-encompassing region for appreciating the natural gifts with which the United States has been endowed (again, mostly by stealing them or seizing them from the lifeless limbs of defeated foes). What better example of this than the Grand Canyon?

In The Exploration of the Colorado River and its Canyons—an account of the US government-sponsored three-month geographic expedition along the Green and Colorado Rivers in 1869—John Wesley Powell said, “You cannot see the Grand Canyon in one view, as if it were a changeless spectacle from which a curtain might be lifted, but to see it, you have to toil from month to month through its labyrinths.” He was certainly right about that. Fortunately for the automotive tourist, there’s a road that shoots due north from Route 66 just east of Williams, Arizona and gets you to a bunch of pretty nice viewing platforms on the canyon’s south rim in less than an hour. Even without months to explore its many intricacies, it’s breathtaking. There’s nothing like it. Evel Knievel probably summed it up best: “You can’t say you’re going to jump the Grand Canyon and then jump some other canyon.”


Image for article titled A Road Trip Down Route 66 Is Corny, But It's Also Necessary
Photo: Benjamin Preston

With such colossal natural features and huge leaps between roadside attractions, the fast car came in handy given my truncated time table. You can see Humphrey’s Peak just as well from a speeding Corvette as you can from a sputtering Okie-mobile. At this point, I liked to put myself in Clark Gable’s expensive shoes (he’s like the George Washington of 66, and has “slept here” pretty much everywhere). Apparently, he drove a ‘49 Jaguar XK 120 on 66 a few times, and I have little doubt that he pushed the car to its advertised top speed here and there. Then I was reminded of my danger by a set of vintage Burma Shave signs near Seligman, Arizona:

“If daisies

Are your

Favorite flower

Keep pushin’ up those



There’s no such thing as Burma Shave anymore, but from the late-’20s until the early-’60s, the signs were set up on the sides of highways all over the country, using evenly spaced five-sign sequences to keep motorists intrigued and awake. The signs started as simple ads, then grew into clever rhymes. By the end of their run, there were quite a few driver safety public service announcements threaded in, like this one you can still see:

“He tried

To cross

As fast train neared

Death didn’t draft him

He volunteered


When I crossed the Colorado River into the torrid, overpriced hell that is Needles, California, the blazing hot hand of Apollo slapped me back to Okie reality. My heart bled for those long-ago refugees, who had struggled over endless miles of indifferent high plains only to arrive at the doorstep of the somehow more inimical Mojave Desert.

The Corvette’s fancy dash thermometer recorded an outside temperature of well over 100 degrees, and even when the mercury fell after sundown and removing the roof seemed like a good idea, I could feel an intense blast of stored-up heat every time I drove beneath a concrete overpass.

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Photo: Benjamin Preston

The further west you travel in California, the more reminders there are that you’re nearing L.A. It starts with In ‘N’ Out Burger sightings, and gradually solidifies into the unyielding wall of tail lights that lets you know you’ve almost made it. This is also where past and present begin to collide. In the middle of the country, where things are spaced further apart, decay is more apparent than on the edges, where real estate costs big money. In these cities like L.A. and Chicago, where every year more and more Americans move from the dwindling middle parts, reminders of the past are easily drowned out amidst the steady, devouring crunch of industry and progress.

Cruising past the restored Wigwam Motel just west of San Bernardino, the concrete teepees (not wigwams at all, in reality) reminded me of Joan Didion’s assessment of interior California’s starkness in Some Dreamers of the Golden Dream, a piece she wrote for the Saturday Evening Post in 1966 about a murder that had occurred nearby. She had listed the motel—“SLEEP IN A WIGWAM – GET MORE FOR YOUR WAMPUM!”—as a landmark when setting the scene:

The San Bernardino Valley lies only an hour east of Los Angeles by way of the San Bernardino Freeway but is in certain ways an alien place: not the coastal California of subtropical twilights and the soft westerlies off the Pacific but a harsher California, haunted by the Mojave just beyond the mountains, devastated by the hot dry Santa Ana wind that comes down through the passes at 100 miles an hour and whines through the Eucalyptus windbreaks and works on the nerves.

By the time I descended into the Los Angeles basin, my patience for old motel and filling station signs had worn thin. The hot desert air had worked on my nerves and I craved, no needed, the cool westerly blowing off the Pacific. It took an hour to crawl the last couple of miles into the parking lot at the foot of the Santa Monica pier, but the benches out on the end of the ferris wheel-topped structure were a fitting reward at the end of a long trip. The setting sun, the soft breeze, the gentle murmur of weekend revelers enjoying the amusement park – it was all a reinforcement of my decision to make California the finish line.

It’s America’s finish line, after all. It’s the promised land. Even if you never get everything that was promised, the illusion is so very sweet, especially when you can eat a burrito and dip your toes into the water at the same time.