The streets that carried the earliest alignment of Route 66 through Springfield, Missouri, took travelers past its central square. There, guidebooks say, Wild Bill Hickok killed a man in a shoot-out, shortly after the Civil War.

That was enough to pull three hungry guys off the highway. As it happens, we were following one guidebook’s advice not to miss the route’s bucolic ramble into the Queen City of the Ozarks, but we could have followed a later alignment that bypassed downtown, long before anyone thought of bypassing 66 altogether. So we steered our Jeep Laredo (did I mention three guys here? We’re going to rent a Tercel?) onto St. Louis Street. We nodded dutifully at the Shrine Mosque, a lovely old theater H.H. Richardson might have built for Shah Jahan, and found a parking lot.

Park Central Square is an arrangement of experiences in concrete and chlorophyll, very midcentury modern, with a waterfall fountain, flower beds and trees and something like a sunken living-room effect. We roamed the park awhile, but, serenaded by nearby construction, we gave up our search for signs of Wild Bill’s showdown with a man who dared to wear a watch Hickok had lost to him in a card game.

We found, instead, a bronze plaque in a flower bed, marking 1992’s 66th anniversary of “the official birthplace of U.S. Highway 66, ‘The Main Street of America.’” In 1926 Springfield found itself at the hinge of the federal scheme to connect Chicago and Los Angeles with links of organic origin, old plank roads and Indian trails, newly spread with concrete and asphalt to expedite the 20th century. It was to be U.S. 60, but Southerners had already started printing maps showing that road going from Virginia to Springfield, so the Chicago-to-LA boosters settled for 66.

Elsewhere on the square is an open bronze book, placed by the University Club of Springfield in 1972, that tells the square’s story up to 1970—Civil War tussles, the courthouse burning down. On the side of the concrete base, a bronze plaque says “ahem” to this earlier chronicle:

ON APRIL 14, 1906, THREE BLACK MEN, HORACE B. DUNCAN, FRED COKER AND WILL ALLEN, WERE LYNCHED WITHOUT A TRIAL

It had to have been a horrid affair. Duncan and Coker, arrested on suspicion of assault, were released from the city jail on an employer’s alibi but then were rearrested and later lynched from the county jail. The crowd came back for Allen, in jail on unrelated charges, and hanged all three men from the square’s central monument, Gottfried Tower, described by the Springfield News-Leader as “an iron structure … with electric lights, an elevated bandstand, and a ‘Welcome’ sign, topped with an iron Statue of Liberty replica.”

Weary of the irony, Springfield removed Gottfried Tower in 1909.

Good Route 66 pilgrims, we started on Michigan Avenue in Chicago. Ron, a former newspaper colleague, and Tony, a freelance broadcast engineer, have traveled widely in their careers—they met at Kandahar Air Base in Afghanistan—and they hatched the idea of driving the remnants of old Route 66. I tagged along, curious about the iconic road in anxious times.

Today its principal freight is memory. It has always hawked ready-made memories to a nation obsessed with collecting them, but today much of its inventory is that very sales history, memories of marketing past. But the route also sells a bygone Americana of sidewalks and front porches and homegrown merchants. John Steinbeck, who drove it to research The Grapes of Wrath, christened it “the mother road,” but the matron of Dust Bowl migrants is more like a grandma docent, leading field-trip tours through the Museum of Postwar America.

Giant was big. “Giant Alert!” our main guidebook warned nearly every page. Rocking chairs and astronauts and arrows, some restored, some decaying, lured Instamatic-armed families from their Bel-Airs and Fairlanes. And so with the Old West. In Oatman, Arizona, at the western end of a segment that twists through desert hills, TV-Western cowboys duked it out along the dusty main drag, while wild burros plodded along beside creeping SUVs.

In Galena, Kansas, a rusty International tow truck guarded the first of several right turns the route takes through the southeast corner of the Sunflower State, for a dozen of its 2,300 miles. At 4 Women on the Route, whose partners installed a café and gift shop in a restored gas station, we learned that the truck inspired the character Mater in the Disney-Pixar animated film Cars. Galena’s story parallels that of the movie, so far minus the happy ending.

Cars are people in Cars. They race while RVs party in the infield and sedans cheer from tiered concrete slabs. When an arrogant racer strands himself in Radiator Springs, he helps its four-wheeled shopkeepers revive their town by pulling traffic from the interstate. The filmmakers did their homework, roaming Route 66, and they adorned the film with vehicles, buildings and signs from the road.

The anthropomorphic conceit, however, highlights our mania for cars, the ways they warp human temperament and shape lives and landscapes. You don’t have to imagine a NASCAR grandstand for 100,000 cars—just picture the real-life parking lot. Figure on four or five parking spaces, roughly 1,600 square feet, per 1,000 square feet of any suburban building. Then count the real-life costs, in treasure and blood, for fuel, and the menace of carbon compounds in the air. Cars’ solution is to get rid of the people.

Its lesson, to slow down and smell the asphalt, is equally thorny. The highway was born of boosterism and eventually succumbed to it. In Route 66: The Mother Road, Michael Wallis relates how Tulsa businessman Cyrus Avery, “the father of Route 66,” used government and private posts to push the idea of a highway to California. “Instead of adopting the traditional northern route, which followed the historic Santa Fe Trail, or the far southern route, the Butterfield Stage line, Avery was successful in establishing yet a third route … that happened to come directly through Avery’s hometown of Tulsa and the state capital, Oklahoma City,” writes Wallis—who, incidentally, voices a character in Cars.

Carrying Dust Bowl Oklahomans to California farms and postwar dreamers to Hollywood, Route 66 quickly became iconic. Nat King Cole had a hit in 1946 with the Bobby Troup song, which hints at the postwar Californiation of America. Route 66 was how you got there, literally and mentally:

Won’t you get hip to this timely tip:

When you make that California trip

Get your kicks on Route 66.

By contrast, the 1960–1964 television series Route 66 had little to do with the road, whose mere designation epitomized the rootless wanderings of two young men in a Corvette, trying not to get anywhere. Although at times the show intimated a dark restiveness, it helped popularize the notion of the journey being the destination. But by then the U.S. was hard at work on the Interstate Highway System, which is about getting somewhere as fast as wheels can carry you.

It was nearly inevitable that later generations of the boosters who built Route 66 would clamor for superhighways.

Purists take weeks—we had two—to cover every stretch of old 66, spurning the interstate. But large stretches of the old road are gone, or impassable, and for many miles it parallels the interstate, offering little more than a bumpier ride at slower speeds. Even guidebooks recommend the interstate at times.

We got off I-40 at Joseph City to see the Jackrabbit Trading Post, home of a giant saddled rabbit in permanent pose. Across the blacktop, a yellow sign with a black rabbit silhouette announced, “Here It Is,” a relic of the days when billboards for miles in each direction touted the stop—Cars planted a version of the sign in Radiator Springs. Inside, a young woman told us business had been slow, a concern echoed elsewhere. The nearby interchange helps keep this landmark alive, but the old sedan with a flat and the shut-off gas pumps were not narrative décor.

Later, we entered Winslow, Arizona, from a forlorn stretch of desert two-lane in search of a more recent landmark. Seizing on a stanza of the Eagles’ early hit, the Jackson Browne-Glenn Frey tune “Take It Easy,” the Standin’ On the Corner in Winslow, Arizona, Park Committee installed a bronze statue of a man with a guitar on a corner and parked a flatbed Ford next to it. They also refurbished a famed Fred Harvey Hotel, but since 1999, the chance to animate a throwaway line from a pop song has drawn thousands from Interstate 40.

The early boosters of Route 66 called it “The Main Street of America,” because it stitched together the centers of cities and towns, and spooled out for travelers a tapestry of local quirks and customs. But the interstate gathers all to its brands, serving up reliably regular chain lodging and meals on the fringes of former towns.

The results of that courtship and abandonment play out along the route. Some towns make the most of it, get grants to refurbish old motels and sell camera-ready memories. State and national nonprofits advocate preservation of Route 66 alignments and attractions. Elsewhere, though, the old gas-ups and trading posts and neon signs molder and collapse.

Springfield, Missouri, is a pivot point for Route 66 and the nation. It casts the route westward, after its southwesterly drift from Chicago. Before long, rolling farmland and forests yield to rock and scrub. And its history echoes the tensions between North and South, black and white. The Route 66 story is, in some ways, as deficient as the history book on Springfield’s square. For one thing, it is largely white, about a time when few minorities enjoyed the middle-class perk of a long road trip. And its laudable linkage of Main Streets eventually led to their desertion. Two builders of those chrome-lined cars have filed for bankruptcy.

It is a stretch to tie the “financial meltdown” to the building of interstates, but the mind-set that pushed us into bigger cars on wider roads to more distant neighborhoods also littered the suburbs of Las Vegas with vacant McMansions. Our postwar enthusiasms collided with unintended consequences, both internal and external. Still forging compromises about our past—sorry we treated many of you so miserably… how about a plaque?—we face furloughs and cutbacks and bankruptcies. We take staycations and layoff-cations. Americans may be forgiven, a little at least, if they feel let down by leaders who sold them a story as untenable as any historical lie.

No doubt some stretches of Route 66 today reprise the Mother Road role of carrying job seekers to new prospects—eastward this time. But the route also beckons the newly disenchanted, not with illusions of bygone America, but with its rejection of homogenous interstate culture.

A week after leaving Chicago, we stopped a little west of Barstow at another guidebook must-see, The Bottle Tree Ranch. Here, Elmer E. Long, a slight man with a long white beard, manages not a ranch but a forest. His yard is filled with metal armatures supporting thousands of colored bottles, and various yard-sale and flea-market finds. We helped him unload from his truck some sort of antique press—he didn’t know, didn’t care. He just cultivates his crystal garden. We chatted and took photos, and as we were leaving, I pulled out my wallet to find a scrap of paper on which to write his name. Long thought I was offering him money and waved me off.

We got our kicks.