For the ultimate summer road trip, take Route 66

In 1926, Route 66 was supposed to be the Main Street of America, stretching from Chicago to L.A. Motoring was exciting, roadhouses were sexy, and motels were about to be invented. Soon, you could find just about anybody chugging along Route 66—movie stars, hobos, families, soldiers, illicit lovers and gangsters looking for anonymity, Dust Bowl migrants, musicians, “tin can tourists” camping by the side of the road. What sprang up around them was pure Americana: neon-signed diners pouring thick malts; Streamline Moderne “motor courts”; wigwams and kitschy trading posts; gas stations that could fix your Ford Fairlane; glittering caves and alligator ranches and caged tigers. Route 66 was about Americans’ worship of motion and ingenuity, their love affair with their cars, the open road’s adventures.

But by the late 1950s, the new interstates had begun to chop up our 2,400-mile Main Street. In 1985, Route 66 was decommissioned.

It wouldn’t die.

Today, the route’s a patchwork of winding roads and bits of freeway, and traveling it is a scavenger hunt that pieces together a bygone America. Siri can’t help you find the Old Road. Without a great map (and there aren’t many), you’re doing breadcrumb navigation, flipping a coin at a four-way and waiting to exclaim with relief when (if) you see the blue-and-white Historic Route 66 sign.

On the Mother Road, you’ll see Aussies, Asians, tons of Brits, and other Europeans. In 2016, a Route 66 festival was held in Germany; another will be held this August in the Czech Republic.

Tourists come to see the real America. Or the old, simpler America. Or the friendly one.

RIVER CITY

It was just outside St. Louis where Bobby Troup’s wife whispered the first line of the song he’d eventually write: “Get your kicks on Route 66.” Nat King Cole sang it, then Chuck Berry, the Rolling Stones, Depeche Mode. Meanwhile, how you “go through St. Looey” was changing. First the (now-Old) Chain of Rocks Bridge was built to carry Route 66 across the Mississippi. Then, in 1932, the county section’s main axis changed from Manchester to Chippewa/Watson and I-44—prompting construction of the Meramec River U.S. 66 Bridge.

That bridge is now surrounded by Route 66 State Park, an idyll with a backstory—dioxin poisoning in Times Beach—that’s even sadder than the disappearance of the storied Coral Court Motel, on Watson Road,  where flashbulbs exploded to capture wealthy wives’ dalliances and the Greenlease kidnappers hid out. Cheer yourself up at Ted Drewes Frozen Custard with a concrete to match the road. Then zoom ahead to another hideout.

Meramec Caverns really would have made a perfect place for Jesse James to disappear, as its showman owner insisted. (The bandit’s lore is preserved at the nearby Jesse James Wax Museum.) The caves form one of the oldest natural wonders along Route 66, and their fragile stalactites and stalagmites survived the boom of owner Lester Dill’s voice as he bragged, “I’ve put more people underground and brought them back alive than anyone else on earth.”

After all that damp dark and hoopla, you’ll need more ice cream: Stop for a malt at the Circle Inn in the town whose water tower says Bourbon.

Follow the “Race to the Rocker!” sign to Cuba, where the highlight is the Wagon Wheel Motel. The 1939 AAA travel directory pronounced its English Tudor Revival cottages (built from brown and ochre Ozark sandstone) “a home away from home…one of the finest courts in the state.”

Cuba has more of those Ozark “rocked” buildings, but the town’s distinction is its vivid murals, re-creating Bette Davis dodging paparazzi, the local banker who owned Cuba’s first Model T, Amelia Earhart’s emergency landing in Cuba in 1928, Cuba’s Gold Star Boys heading off to World War II on the Blue Bonnet train…

Fill up at the vintage Phillips 66 station—which will make you want one of the old service station signs for sale at Bob’s Gasoline Alley. The fuel will propel you to Fanning and that giant rocker you’re racing toward, painted black and brick orange with a Route 66 shield on its high back. Once you’ve shaken your head over America’s love of giant everything, head for the Rosati Winery. In the right season, Concord grape stands will line the road.

When you get to Rolla, head for the half-scale Stonehenge. Imagine the Druids paling as they watched students at Rolla’s School of Mining carve granite with pressurized water jets, then align the structure with the summer solstice by computer. Shake the contrast at dueling trading posts: the Totem Pole, whose owner brags that it’s the oldest mom-and-pop souvenir store along Missouri’s Route 66, and the Mule (whose ears still wiggle on the sign). The Mule Trading Post was bought by a new owner in January and is undergoing renovation, but an outpost is still open if you’re in need of, say, a walking stick with a carved white buffalo head. “One summer they had a guest book, and there were people from 58 countries,” says Betty Karr, who works next door at the Mule Tobacco Barn. What brings them? “Nostalgia. The good old days. Simple.”

HOOKER CUT

Now hop on i-44 for a stretch, to the Jerome exit. The drive’s getting beautiful, edged by crenellated rock, the hills dotted with pine trees. Between Doolittle and Arlington, if you want a melancholy adventure, detour to John’s Modern Cabins, at the end of the Arlington outer road, where the forest is slowly consuming a 1930s cabin court. Down the road a ways, Vernelle’s Motel, opened in 1938, has finally given up the ghost(s). And Arlington’s luxe Stony Dell Resort is barely visible anymore. While you’re feeling wistful, the towns of Clementine and Hooker were once called Basketville, because locals sold handmade baskets along the road.

Shake off the mood: You’re about to drive through the 90-foot Hooker Cut that sliced Route 66’s first four-lane through the bluffs when the new Fort Leonard Wood’s traffic demanded a solution. (More than 300,000 soldiers would pass through its gates by the end of World War II.) Leave the new Route 66 for Teardrop Road, heading for the Devils Elbow bridge across the dark-green Big Piney River, the prettiest spot you’ll see on this journey. Soak in the view from the 1923 steel-truss bridge down the bluffs and across the river to the Clark National Forest. Named by cursing lumberjacks fighting to float rafts piled high with logs around a sharp bend in the Big Piney, Devils Elbow was dubbed one of the Seven Beauty Spots in Missouri in 1942.

St. Robert’s brightly painted commercial district, originally named for a planet but coopted by its inevitable marketing slogans. There’s a fake rocket outside, aimed at a ’60s-style exploding star, but the signs smirk, “Thank you for keeping Uranus clean,” and the shopkeepers chant, “The best fudge comes from Uranus.” You can buy guns and ammo here, too, or do archery, or throw axes at the Uranus AxeHole, or get a tattoo at Skin City, or Escape Uranus in the escape room, or visit the Mission Outpost Outdoor Outfitters, built as a replica of a stockade. Alas, the burlesque show has closed. (A nearby billboard reads, “Pornography pollutes body * soul * mind.”)

Brace for kitsch: You’re about to pull into

Inside the Uranus Fudge Factory are curiosities in old wooden display cabinets—a two-headed rabbit, a rattlesnake, a fish/man thing that defies description. On the walls hang bags of marbles, nose flutes and bright kazoos, a hand buzzer, a bendable Gumby, a whoopee cushion, an old-timey horseshoe puzzle, and Pez.

“I especially love the big old burly guys who come in, and you say, ‘Thank you for picking Uranus, guys,’” giggles cashier Amanda Miller. She and coworker Bailey Ploch love the pure fun of their jobs. “Honestly,” says Ploch, “I don’t think people really know the real meaning of Route 66.”

There is no single meaning. Choose your own adventure. Just be careful not to get so candied up (the fudge really is good, even the sugar-free stuff) that you wind up negotiating for freedom at Fort Leonard Wood. One wrong turn and the road turns one-way without warning.

BIRTHPLACE OF ROUTE 66

The next major metropolis is Lebanon, home of the Munger Moss Motel. It’s classic auto court style—carports and a central courtyard—and the neon sign is still lit for business. Expect a crowd at the Route 66 Festival, June 15–17 (classic cars welcome).

Next, you need to go to the library—inside, past the gift shop, is the new Route 66 Museum. You’ll find black-and-white–checkered tile floors and all the paraphernalia of early motoring: dusters, veils, caps, maps, and picnic gear.  

At the immaculate Conway Rest Area, look for little Route 66 picnic gazebos, each decorated as a different landmark. Then move on to Strafford to see more than 600 animals at Wild Animal Safari, founded in 1971 by Pat Jones, father of Dallas Cowboys owner Jerry Jones. It’s home to a white Bengal tiger, African lions, aoudad, nilgai, camels, baboons, spider monkeys…

Back on the road, you’ll see signs for cigarettes, guns, rockets, adult superstores, firecrackers, cars, motorcycles—explosives of all kinds—interspersed with signs of Christian devotion. Asked about the contrast between, say, the Lion’s Den adult superstore and the Baptist billboard next to it, one proprietor smiles and says: “Well, it’s highly individualistic. This is not a homogeneous trail.”

Route 66’s attractions tend to be superlatives—the biggest praying hands, the wildest alligators, the fastest Harleys—but the people you meet are just the opposite: middle-of-the-road and Midwestern-friendly, shrugging off their neighbors’ quirks and differing values.

Arrive in Springfield, where Route 66 was christened back in 1926. Cyrus Avery, a former Missourian who served on the federal interstate commission, worked with John Woodruff of Springfield to map out a diagonal route across the country. They used everything: existing roads, Osage trails, paths blazed by early settlers... When the route couldn’t be numbered 60, because it wasn’t a clean east–west like the other new interstates, the feds suggested 62, but that just didn’t have a good ring to it. Avery sent a telegram from the Colonial Hotel in Springfield, firmly requesting 66 instead.

Today, Springfield does its role proud. It’s preserved a curb-service Steak ’n Shake from 1962; squint as you order, and JFK could still be alive. The Gillioz Theatre, one of the first in the Midwest to show talkies and Technicolor, has been restored to its 1926 Spanish Colonial Revival splendor, with Moroccan details to boot. Every square foot’s ornamented, and the structure’s so solid, it would have cost as much to tear it down. Besides, how do you destroy a place that hosted singalongs during the Depression to keep up people’s spirits? It’s said that Elvis even sneaked over between performances at the Abou Ben Adhem Shrine Mosque.

What has been destroyed, alas, is Red’s Giant Hamburg, which lost its “er” early on to clear the power lines. Home of the first drive-up restaurant window, Red’s twice graced the pages of Rolling Stone. You can still see the 1945 cabins of the Rock Fountain Court, though, and the Route 66 Car Museum, where Brass Era horseless carriages share their home with Batman’s Gotham cruiser.

THE GHOST ROAD

Once you’re back on the road—a quieter section, winding past a half-dozen faded towns—it sinks in just how different this sort of road trip is. Cows aren’t just dark specks dotting a green blur; you can see them—markings, sheen, placid expression. And if you want to stop to chat or explore, you just…stop.

In Avilla, you stop to see the post office that had a Bonnie and Clyde–style robbery during the Depression. In Paris Springs, you stop at the Gay Parita, a restored 1930s stucco Sinclair that’s an eclectic museum/store.Then you glide into Carthage, the self-proclaimed Crossroads of America. It’s here that Route 66 intersects with the old Jefferson Highway that stretched from Winnipeg to New Orleans.

You’re tired by now, and hungry. Save a trip to Red Oak II—a ghost town collected piece by piece—for tomorrow. Save the Battle of Carthage State Historic Site, too: You’ll walk a field essentially unchanged since 1861. Tomorrow evening, you watch whatever’s playing at the 66 Drive-In, built in 1949 and one of the few still in operation. Then it’ll only be 15 minutes to Joplin, where you can check out the Route 66 Mural Park. Pay homage to the now-closed Dale’s Ole 66 Barber Shop and grab a bowl of chili at Fred & Red.

But for now, you’re in Carthage, and you’re exhausted. Check into the Art Deco Boots Court Motel, which is being slowly, lovingly restored by a historian and her sister. Onsite manager Deborah Real will tell you how Arthur and Ida Boots built the place in 1939, curving strips of glassy black tile around the white stucco and charging a whopping $2.50 a night “to keep out the riffraff.” In 2013, one of the legends of Route 66, Tattoo Man, strolled in. (Legally he’s Ron Jones, but “there’s an entire trip down Route 66 all over his person,” Real explains.) He said, “I know you girls want that sign to go back to Boots Court. I’ll pay.” If you’re lucky, Real will give you No. 10, one of the two rooms where Clark Gable stayed. (He had an Army buddy from Carthage.) Real will have the vintage radio playing, and over “Boogie Woogie Bugle Boy” she’ll tell you that the glowing hardwood floor was carefully cleaned and varnished to preserve the wear. You’re stepping where Gable did that June night in 1947 when he “retired early,” disappointing the locals.

Come morning, walk to the square to admire the magnificent Jasper County Courthouse. But first, stop at CD’s Pancake Hut, where owner Wanda Bauth turns out the fluffiest of pancakes and chats with tourists from all over the world. “Great Britain sends a lot of ’em,” she says, sad to disappoint them by having only one kind of tea. “They say, ‘This is such a friendly place.’ They want to see the people in the hometowns and hear about how things used to be.”

Which is how things still are, on the road that will not die.