I’ve been told many times that the best way to see America is to drive across it. You can look at as many maps as you want, but there are things about its mammoth scale that can’t be conveyed in two dimensions. While there are a lot of stretches of highway that can help you understand that scale, there is no path more lauded, more steeped in American history and culture, than the one John Steinbeck nicknamed the Mother Road: Route 66.
Stretching from Chicago (where I was born) to Los Angeles (where I now live), Route 66 was first established in 1926. In its early years, it served as a thoroughfare for truckers, an escape route for Dust Bowl farmers, and a boon for local businesses. After it became the country’s first fully paved highway in 1938, vacationers began traveling its fresh concrete roads in hopes of seeing California for the first time. As time passed, larger interstate highways sprung up around Route 66, and eventually it was stripped of its highway status in 1985.
These days, the best way to know you’re on Route 66 is by paying attention to the quality of the road beneath you. The real 66 is bumpy, unkempt, and rife with weed-filled cracks. The more the road resembles the regular highway, the more likely it is you’ve veered off course. Modern interstates are bright, sterile, and with little to look at besides ads. By comparison, Route 66 makes you feel an intimate connection to the town centers, natural wonders, and giant statues of Paul Bunyan holding a hotdog you might pass by. If I was looking for some insight into the country, even as it lurched toward an election that could drastically affect its future, this was the place to do it.
Courtesy of Dan Sheehan
Oct. 10, 2024: Chicago
Joined by my old friend Evan, a fellow 30-something Americana enthusiast who has also managed to somehow carve out 10 days for a drive, we set out that morning from the newly minted Route 66 Starting Point on Michigan Avenue, across the street from the Art Institute. We’re in high spirits, with me behind the wheel of a rented Volvo SUV. I had waved off the extra time it would take to return to the rental lot and add Evan to the list of permissible drivers, saving about 20 minutes but dooming myself to 2,500 miles behind the wheel. This decision seemed to baffle Evan, but I was excited to drive the entirety of the road myself.
A couple hours later we find ourselves in the town of Pontiac, home to the Illinois Route 66 Hall of Fame. There, we’re greeted by a friendly older woman. She asks where we’d come from and when I tell her Chicago, she playfully throws her hands up in a “don’t shoot!” gesture. She then smiles and reassures me that she actually loves Chicago. “You know my favorite building in Chicago?” she asks, pausing for effect. “That Trump tower.” I try to figure out if this is some sort of political litmus test but her expectant smile is impossible to read. We make a diplomatic exit and take a quick look at the models of classic cars and miniaturized gas stations and get back on the road.
Later that night, at a Route 66-themed corn dog restaurant, I look at the kitsch on the walls. There are antique license plates, signs from restaurants long closed, and photographs of small towns that’ve been rendered unrecognizable by the decline that followed the route’s decommissioning. This window into America’s past is part of the appeal of driving Route 66. As someone born in the 1990s, America’s “good ol’ days” have always been a faraway concept, like stories of your dad’s Grateful Dead years, or tales of original-recipe Four Loko. I assumed it was exaggerated to some extent, but I was beginning to get a sense of who that exaggeration benefitted.
In the absence of the steady stream of travelers it once boasted, the businesses that remain on Route 66 have clearly survived by marketing to nostalgia obsessives, selling an image of the past that they find comforting. That image is one absent of modern complexity. There are no phones, emails, or social media. But, much to the delight of the MAGA crowd, it’s also an image absent of modern progress. It’s populated largely by white people, most of whom are grouped off into tidy nuclear families. The cars are candy-colored classics and the cops wear crisp blue shirts instead of riot gear. Anyone with a history book knows this isn’t the true story of America and anyone who’s read The Grapes Of Wrath can tell you that it’s not even the full story of Route 66. But it’s a story people like and as the real world gets scarier, it’s a story people will pay to have told to them.
Oct. 11: Uranus, Missouri
Evan and I spend the day driving through Missouri, haunted by billboards for Uranus, a town founded in 2013 by Louie Keen, a man with a fistful of cash and a penchant for scatological humor. When we arrive, though, Uranus turns out to not be a town at all, but a stylized strip mall made to look like an old frontier main street, and Keen has fashioned himself into a larger-than-life character known as the “Mayor of Uranus” who wears an American flag-patterned suit and patrols the streets — or rather, street. While we didn’t run into him during our visit, his presence on various posters and merchandise made him hard to miss.
As we walk into the general store, a cheery employee bellows, “Welcome to URANUS,” really punching that last syllable. Perusing the store’s shelves, there’s the usual lineup of Route 66 merch alongside a host of shirts bearing new and terrifying puns. A calendar featuring Keen dressed up in his mayoral outfit promises to “Make Uranus Great Again.” Their fudge is as “serious as fudgin’ the presidential election.” My nose wrinkles as I connect the dots. Were these little references to Trump only there because they helped sell more merchandise? Or has Route 66 been so completely co-opted by the right that the two could no longer be untangled?
Oct. 12: Catoosa, Oklahoma
The next morning, we get up early to check out the Blue Whale of Catoosa, a 20-foot high sculpture built in the early 1970s by a man named Hugh Davis as a gift for his wife. The whale is a cartoonish bright blue, and sits on an idyllic pond full of fish and turtles. When it was completed, it drew such a crowd that the family expanded the space and opened it up to the public. “Blessings were showered upon the Davises during the time they operated the Blue Whale,” a sign at the property reads. “No one was seriously injured, no one ever sued, no one was ever bitten by a snake. It was a good time, it was a good place.”
There are plenty of examples along Route 66 of people putting history behind plexiglass and charging tourists for the opportunity to gawk. Here, I find myself moved by the story of a man in his later years building something that brought people joy and deciding to share it with the public. Hugh died a long time ago, but anyone who passes his creation can still freely sit on the edges of its pond and fish. As we walk in, two brothers are doing just that.
Courtesy of Dan Sheehan
With the place mostly to ourselves, we get our pictures of the whale and head back to the car. But just as we start to leave, a massive pickup truck barrels towards the lot with two huge Trump flags hanging off its cab. A second car, done up in similar fashion, comes up behind it. Then a third. Before long, the parking lot has at least 10 cars outfitted in Trump regalia. Their passengers get out, each of them clad in various combinations of red, white, and blue. Is it possible that this, of all places, is where Trump has decided to hold a campaign event today? As each new car pulls up, more excited Trump supporters pour out. Their shared fanaticism feels like a ritual, as though Trump himself might rise from the lake.
Luckily, the former president isn’t conjured, but the Blue Whale is smiling as an older man addresses the growing crowd. He begins speaking of ejecting the many people in our country whom he has deemed undeserving of his bounty. He’s full of angry passion, but without a microphone, his voice refuses to carry more than about 20 or 30 feet. He quickly loses the attention of the crowd. I start to wonder where they’d be holding the impromptu rally if Hugh Davis had chosen to keep his property’s borders closed.
Oct. 12: Chandler, Oklahoma
Jerry McLanahan is the man behind the most notable Route 66 guide in print, a labor of love so meticulous and well considered that Evan and I came to judge the quality of the gift shops we visited by whether or not they carried it. The guide provides an open invitation to its author’s gallery, so of course we plan a stop. Before we even introduce ourselves, he asks for our copy. With great efficiency, he flips through and marks various detours and road closings.
We get to chatting. He tells us about a small network of enthusiasts who pooled their efforts to investigate which pieces of old road were once part of the route. Route 66 has had many iterations over the years and there’s ongoing debate. Jerry tells us about a man who carries a small pickaxe with him like a modern archaeologist, chipping at the edges of a stretch of highway in the hopes of knocking away the asphalt and discovering original Route 66 concrete underneath.
He talks more about his process, the many trips up and down the road that are necessary for maintaining his guide. He smiles. “You’re gonna chase a lot of rabbits,” he tells us. “You’re gonna waste a lot of time.”
Oct. 13: Texas Panhandle
After spending a night in Amarillo over some big Texas beers, we make for Tucumcari. With only two hours of road to cover, we decide to lean heavily into roadside attractions for the day. The first we stumble across is the Second Amendment Cowboy, a giant statue of a cowboy whose yellow shirt bears the words “2nd Amendment Cowboy.” Surprisingly, the statue doesn’t have a gun in hand or even in holster, but he canonically loves the fact that he could.
Despite the overt right-wing leanings of our latest giant attraction, I find myself more at ease with the way Texas presents its unique brand of nationalism. Texas is less concerned with nostalgia for America’s past as it is with enthusiasm for itself. I see the Texas flag far more than the American one and its message is far simpler: You are in Texas, with all that that entails.
That’s in stark contrast to my run-ins with the American flag over the course of the trip thus far, which have left me more conflicted. Whether I’d seen it flying on the back of a pickup truck or stitched into a novelty suit for a mayor, the flag had begun to carry an ominous aura. Flags are just symbols, shortcuts you can use to recognize someone’s affiliation. And while the American right wrapping themselves in it was nothing new, the flag had become so thoroughly branded around such a specific set of beliefs that it felt like it no longer represented anything else. When an authoritarian movement gets its claws in a flag, it doesn’t tend to walk away unscathed.
Just before our trip began, a group of St. Louis Neo Nazis had draped swastikas on an overpass in an act of pre-election saber rattling. Now, Evan and I see another overpass gathering. This group waves no swastikas, only American flags. The lack of hate symbols comes as a relief to us, but the gesture seems ominous. We have no reason to assume they are Nazis, but if the sight of 10 men waving my country’s flag at oncoming traffic is meant to bring me comfort, it fails.
Courtesy of Dan Sheehan
Oct. 14: New Mexico
We make a quick stop at the Blue Hole of Santa Rosa, an 80-foot-deep natural watering hole with crystal clear water that flows steadily enough to fully replace itself four times a day. When I hear the name, I brace myself — after Uranus, I’m not sure I can physically handle any more puns. But I’m delighted to find that the Blue Hole is idyllic, with just a couple small groups basking in the Monday morning sun. Five young Spanish-speaking friends razz each other to jump in from the rocky ledge. One of them goes for it with a spectacular cannonball, and when he emerges with a massive grin, even strangers cheer for him. A nearby older woman with a thick Texan drawl yells, “Bien trabajo!” Her accent makes it sound like a song. I imagine what this place would’ve looked like to Route 66 visitors in the 1920s, after days of driving through prairies and deserts. I see everyone smiling, swimming, and laughing with strangers.
This is where I choose to wear my rose colored glasses, at a place where I can see people of different backgrounds who’d likely never have given each other this much attention otherwise, bonding over how nice it is to sit in the sun outside a clear blue pool.
Next, while taking pictures of autumnal Cottonwood trees in Pecos National Historical Park, we see a ranger giving a free tour. Her name is Leah, and we listen as she tells us about the Battle of Glorieta Pass in which Union soldiers successfully pushed back a Confederate incursion into New Mexico. This forced the Confederate soldiers, by this point mostly just wayward teenagers, to retreat back through Santa Fe, begging for any aid the town they’d just threatened could spare. Leah tells us about the lone woman who advocated for helping them, declaring that each one was someone’s son and deserved a bit of human decency.
Leah closes by asking us what we’d have done if we found ourselves in the same situation. Would we have been able to show grace to our enemies? Could we feel sympathy for scared kids in the wrong uniforms? “You don’t know what moment you live in,” she says. “What we’re living before, during, and after. We have to choose for ourselves how to react.” The audience is silent. Then she sends us all on our way, spellbound.
A few hours later, we arrive at Santa Fe Plaza to find it filled with rows of stalls selling food and art. As tribal music floats through the air, we realize how thoroughly a week on the road has fried our sense of time. It’s Indigenous People’s Day. The event, known as the Intertribal Powwow, is a day of celebration for Santa Fe’s sizable native population. We watch and take the chance to stretch our legs, eat good food, and enjoy the company of excited strangers.
During the closing ceremonies, I see a man wearing a hybrid Blue Lives Matter/Confederate Flag shirt solemnly remove his hat as an elder finishes his speech. No one had asked for the gesture, something in him had just clicked and decided it was the right thing to do. The instinct towards respect was still in there, like concrete beneath asphalt.
When we roll into Gallup for the night, I feel better about humanity’s chances than I had in days.
Then came Arizona.
Oct. 15-17: Arizona
We pass by the roadside ghost town of Twin Arrows, where Hopi and Navajo settlements date back nearly 1,000 years. The land was stolen by Spanish settlers, becoming part of Mexico and then the United States. A railroad was built along old pioneer wagon trails, and Route 66 was built along the railroad. At the height of the route’s prominence, it brought significant traffic to a series of gas stations and general stores that lured travelers off the road with two giant arrow sculptures that appeared stuck in the ground.
When I-40 became the preferred thoroughfare, the businesses were abandoned. Now, the empty buildings sit dilapidated and covered in graffiti and one of the arrow sculptures has gone missing. The graffiti expresses anger at the fraught nature of this particular plot, which sits on tribal land, but is technically owned by the state of Arizona. As we make our way down the route, we are once again confronted by kitschy, white-owned stores shaped like teepees with names like “Indian Trading Post.”
In the late afternoon, we take a detour to Sedona, a confusing bastion of concentrated wealth tucked into a place so beautiful that industrialized man should never have been allowed to build there. Now, it’s overloaded with folksy kitsch, crystals, and wellness books sold alongside $25 burgers and Life Is Good sweatpants. The entire town feels like it only exists because some developer got their hands on it before anyone else got a chance to designate it a national park. One of the bigger subdivisions, in a clear attempt to avoid infighting between residents, has aggregated the entire community’s election lawn signs into one section near the gated entryway. One giant sign reads, in a chunky 1960s font, “Make Love, Not War – Trump/Vance.”
On a dirt road outside Flagstaff, we stop at a combination gas station/post office to send a few postcards and fuel up. Inside, I run into a German woman who says that she’s been biking the entirety of the route for nearly two months, only taking cars when she hits a span with too few places to get water or camp. “It’s very different from driving,” says. “You meet more people, stop in more places.” While it kind of feels like she’s dunking on me, I can’t disagree with a woman twice my age who’s on a 2,500-mile bike ride. I ask her what gave her the idea and she smiles. “I am retired. I can do anything.”
As I head back to the car, I think about how much I miss my wife and cat after just a week and change on the road, let alone months of rigorous cycling and camping. I do a little math in my head and realize that at her current rate of travel, the German woman may wind up finishing her journey in a very different country from the one she set out in.
Oct. 19: Oatman, Arizona
After a brief stop in Seligman, Arizona — and a visit to a not-very-veiled souvenir shop called Return to the ‘50s — we find ourselves in Oatman.
Oatman was a gold mining camp founded in the early 1900s and named after Olive Oatman, a girl who’d been taken by the Mojave people and lived among them for years before returning to white society. At the time, the story was dramatized and used to stoke hatred towards America’s indigenous populations. It clearly struck a chord with the town’s founder, as he had no personal connection to its namesake — he simply chose to name a town after the early 20th Century equivalent of a viral Facebook post.
With its Gold Rush days long behind it, Oatman’s 2024 economy is a little more precarious. On paper, a visit to Oatman lets tourists experience a preserved Wild West town. In practice, it’s a place to watch people avoid getting bit by donkeys. This is because Oatman’s primary tourist attraction is the multitude of loose, wild burrows that wander its streets, bouncing from tourist to tourist and gorging on feed that is conveniently sold for $5 a bag.
If the primary pillar of the town’s economy is wild donkeys, the second is Donald Trump. There isn’t a single store on Oatman’s main street that hasn’t found a way to promote Trump merch. One of the town’s restaurants displays a massive flag featuring the notorious photo of Trump in the aftermath of his assassination attempt, his fist rising to the sky. Another hangs a 13-starred colonial American flag. Twisted Sister blasts from speakers on the street and the tourists bob their heads along. Self-sufficient, homogenous, and isolated, this seems to be the realized dream of modern conservatism. Plus donkeys.
Oct. 19: California
Maybe it’s trip fatigue setting in, maybe Oatman broke something in us, or maybe it was just that I now know what lurked behind it, but Route 66’s kitschiness has become repulsive to me. Americana has been coded with Trumpism, and each additional dose of it makes me more and more concerned for the world I’ll be waking up in after this trip ends. As we cross the Colorado River into California, I can feel the pull of home, the warm familiarity of my bubble returning. People would be wearing my preferred brands of t-shirt here, though we’d soon see how much good it’d do us.
As we make our way to Santa Monica to pick up our certificates of completion, my mind drifts to everything I’d seen over the last 10 days. Yes, Route 66 is a historical landmark. Its lifespan tells the story of the 20th century. Its winding, disjointed, miles contain more interesting people and places than even an ambitious guidebook writer could ever hope to chronicle. But the route’s very existence was once an investment in the new, an expression of our desire to go somewhere. Route 66 in its prime promised that there was more and that we could be part of it. It promised a future.
As I often remarked to Evan on the trip, I couldn’t imagine driving the road the other way, as we’d seen some folks doing. Route 66 should be experienced westward, seeing the sun set over a series of new horizons. I worry about the next horizon. The only future being promised now is a warped refraction of our own idealized past.
I don’t know what will happen from here, but I did manage to find some solace on Route 66. If further descent into chaos is our fate, if the next few years try to bury us, we will need to become those modern archaeologists, sneaking into the night to chip away at that asphalt in hopes of finding the concrete underneath. When we do, we’ll know where the road behind us really was. Maybe then, the path forward will be a little clearer.
