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Route 66: My Journey Discovering the Most Storied Hotels on America’s Mother Road

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The nostalgia of Route 66 took me by surprise the first time I wound through dusty small towns, passing kitschy roadside attractions flashing the past in isolated incarnations. Long fascinated by mesmerizing tales of the Mother Road before it was even paved in 1926, I knew the stories dug much deeper than flashing neon signs, vintage motels, hot-rod museums, and rubber rattlesnakes hawked from roadside trading posts. After all, Steinbeck’s epic Depression-era novel “The Grapes of Wrath” placed its destitute sharecropper family on the same route as they escaped the Dust Bowl in the 1920s.

However, it was impossible to resist the lure of happier times depicted in the classic roadside diners, gas stations and storied hotels along this “Main Street of America.” Stretching for 2,448 miles from Chicago to the Santa Monica Pier in Los Angeles, it’s where the iconic American road trip was born. Slicing through fertile farmlands, majestic purple mountains, natural caverns, painted deserts and the golden sands of California, it’s an astounding journey through decades of America’s history, heart and heritage

After renting a Mustang in homage to the thousands of Ford Model T’s once traversing the road before me, it was time to download the famous Nat King Cole song and “get my kicks on Route 66.”

“If you ever plan to motor west 
Travel my way, take the highway that is best 
Get your kicks on Route 66″

(Recorded by: Nat King Cole, Bing Crosby, Chuck Berry, the Rolling Stones, Depeche Mode and John Mayer)

Kicking it off at Palmer House Chicago

Although I chose to start my Route 66 journey in Oklahoma for the deeply storied westward portion, many diehard Mother Road devotees kick things off at the signposted starting point in downtown Chicago. At first glance, it’s hard to reconcile the thumping city beat of modern-day Chicago to the laidback retro expectations of Historic Route 66. But a night at the Palmer House Hilton hotel quickly takes things tumbling back to bygone days.

Palmer House perches just steps from the sign marking the official beginning of Historic Route 66 and is the oldest hotel in Chicago as well as the oldest continually operating hotel in America. Potter Palmer built the hotel as an extravagant wedding gift for his bride, Bertha, with a grand opening in 1871 and again two years later after the Great Chicago Fire forced an even grander reincarnation. By the time Route 66 opened for business in 1926, Palmer House had already established itself as the “parlor of Chicago” and gathering spot for the society’s movers and shakers.

Palmer House was (and still is) the stomping grounds for a parade of presidents, film stars, business tycoons and literary masters such as Charles Dickens, Oscar Wilde and Mark Twain, who served as emcee for a big bash in 1879 honoring President Ulysses S. Grant. The hotel’s notorious Empire Room went on to host entertainers such as Frank Sinatra, Louis Armstrong and Ella Fitzgerald and to launch the careers of Liberace and Tony Bennett.

Although the exquisite marble, garnet-draped chandeliers and French paintings of Palmer House may seem incongruous with the humble roadside motels one encounters on Route 66, it actually portrays the dichotomies involved in the forward movement of a changing country. At the end of World War II, the notion of upward mobility pulled thousands of new automobile owners onto Route 66, pushing the boundaries of “Americana” from the Rust Belt of the east to the Sun Belt of the west.

Read reviews of Palmer House Chicago on TripAdvisor

Oklahoma: Dust Bowl and the Road to Opportunity

When I picked up Route 66 in Oklahoma, it somehow seemed okay that I was driving a hot-red Mustang with a copy of Steinbeck’s “Grapes of Wrath” riding shotgun in the front passenger seat beside me. In some ways, it was the incarnation of a twisted history that included the inconceivable losses of ordinary Americans during the Great Depression and Dust Bowl – while also embodying the American spirit of recovery, resilience and hope.

The migration of broken dreams along Route 66 for an entire decade was chronicled in Steinbeck’s Pulitzer Prize-winning story of the tenant-farming Joad family who lost their land in Oklahoma to drought, poverty and foreclosure. Representing the hundreds of thousands of real-life families in the Plains states who made their way along Route 66 to California in search of a better life, the Joad family faced hardships that were inconceivable to those who hit the same highway in later years.

But one thing remained consistent with Route 66: it was a path to opportunity. The endless number of motels, filling stations, cafes and whacky attractions that cropped up over the years were isolated pockets of individual ingenuity and an opportunity to re-write the tragic stories of America’s Highway during the westward migration of the 1930s. The automobile was a big part of that recovery – and so I revved up my Mustang all these decades later and hit the highway of America’s history.

Campbell Hotel

Just two years before the stock market crash ushered in the Great Depression, Campbell Hotel opened its door as the Casa Loma Hotel, an upscale alternative for travelers along the new Route 66. The Spanish colonial revival architecture featured terra-cotta detailing and carved parapets, making it a showpiece structure for the city. After tumbling under economic adversity, it was reimagined in 2011 by 40 local designers unleashing their creativity throughout the hotel. The 26 themed guest rooms of Campbell Hotel once again offer a unique slumber party for today’s travelers on Route 66.

I opted for Room 223, a rustic-chic suite filled with memorabilia from up and down the Mother Road itself. Other suites reflect period Oklahoma culture, including the Tulsa Art Deco suite, Oil Baron’s suite commemorating the oil strike of 1905, and the Leon Russell Room featuring a grand piano headboard in tribute to the musician and inventor of music’s Tulsa Sound. 

Read reviews of Campbell Hotel on TripAdvisor.

Texas: Big Texan Steak Steak Ranch & Hotel

Texas really is as big as its legends, with Route 66 on … and on … and on through the Panhandle. That’s why the gimmicky leftover road tricks are thrilling when they pop up out of nowhere. Case in point: towers that seem to have little function other than attracting attention. Fortunately, the first two Texas towers piercing the skyline are worth the exit into Shamrock to see the film location for Ramones Garage in the movie “Cars.” It’s also home to the historic art deco U-Drop Inn dating back to 1936. In its heyday, it was called the “swankiest of swank eating places” on Route 66.  

There was no mistaking that I’d reached my destination for the night when I spied an enormous steer named Big Moo, a skyscraping 15-foot cowboy boot, and the ‘Big Tex Rex’ 27-foot-tall goofy dinosaur. I had arrived at the Big Texan Steak Ranch, an institution from the 1960s where claims of “I’m so hungry, I could eat a whole cow” are rewarded with a free 72-ounce steak if you can eat the whole thing in one hour (along with a shrimp cocktail, baked potato, salad and a roll with butter).

And yep, people try it all the time, with a count of roughly 50,000 to date and 9,000 successful gobblers. Before checking into my room, I watched as a proud young cowboy strode up to a raised platform draped in the American and Texan flags and flanked by two garbage cans. A cattle skull mounted behind the table glowed with revengeful red lights simmering in empty eye sockets as the clock ticked off the seconds and the crowd cheered and jeered. He lasted a total of 24 minutes before forfeiting his prepaid $72 and skedaddling out the back door.

I ambled over to the Big Texan Motel next door and settled into the replica of an Old West gunslinger town with a swimming pool shaped like the state of Texas. The Big Texan complex relocated in the 1970s from Route 66 to its new location nearby, just off I-40.

My last stop before driving out of Texas was the eclectic art installation known as Cadillac Ranch featuring ten half-submerged Caddies in the desert off Highway 66, lined up in an angle mimicking the Great Pyramid of Giza. They follow a time succession of the Cadillac tail fin from the Club Sedan of 1948 to the Sedan de Ville of 1963.

Read reviews of the Big Texan Motel and Big Texan Steak Ranch

New Mexico: Tucumcari and The Motel Safari

At least 400 miles of Route 66 stretch through the mountains, plateaus and metro centers of New Mexico, a land steeped in Indian and Spanish culture spanning centuries. I beelined for the storied town of Tucumcari and its astounding collection of neon-lit vintage motels still welcoming travelers for decades after their debut along the Mother Road.

After quick stops by the classic Blue Swallow Motel and Roadrunner Lodge Motel along the neon-washed roadway at twilight, I succumbed to the lure of a giant camel outside the Motel Safari. Designed in the mid-century Doo Wop architectural style, the Safari showcases its original geometric camel-laden sign, lighted metal cylinders and stacked-brick façade. Guest rooms are chockful of historic Route 66 photos and trinkets, but I opted to sleep in the Rawhide Suite and dream of Rowdy Yates, the character from the hit television series played by a young and relatively unknown Clint Eastwood.

Santa Rosa to Gallup

It’s considered a sacrilege to miss some of the stops between Santa Rosa and my next hotel in Gallup, including the Route 66 Auto Museum with 30 classic cruisers curated by Bozo Cordova. The Blue Hole of Santa Rosa, a geological phenomenon with a cavity depth of 80 feet, dares travelers to don scuba gear, while the Sky City detour takes you to an ancient 12th-century adobe pueblo teetering on a bluff. Just west of Grants, the Continental Divide is marked by a collection of Indian trading posts selling everything from moccasins to turquoise jewelry and jackalope postcards.

El Rancho Hotel

Who knew that New Mexico was ever considered an annex of Hollywood, with the El Rancho Hotel on Route 66 being dubbed the “Home of the Movie Stars”? It opened in 1937 with wagon-wheel décor and an Old West ambiance that’s hard to ignore. Not that I wanted to, even though I’d already been traveling for days through a timeless rendition of cowboy country.

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But Gallup has a decidedly glitterized element lacking in other southwestern cities, no doubt cultivated by the Hollywood elite who descended on the El Rancho Hotel in the 1940s and 50s while filming more than 100 western movies such as “Billy the Kid,” “Four Faces West” and “Ace in the Hole.” After checking in at the front desk, I was well aware that I’d be sleeping in rooms once occupied by the likes of John Wayne, Humphrey Bogart, Katherine Hepburn, Doris Day, Joan Crawford and Ronald Reagan.

Gallup is not only about movie stars, as at least a third of its population has Native American heritage from the Hopi, Navajo and Zuni tribes. The El Rancho Hotel contributes to the preservation of native culture by selling Navajo rugs and silverwork jewelry as well as Hopi Kachina dolls and Zuni inlaid stone art.

Read reviews of El Rancho Hotel on TripAdvisor

Arizona: Wigwam Motel, Grand Canyon and Hotel Monte Vista

Arizona’s stretch of the old Route 66 plunges beneath I-40, dropping me deep into the Petrified Forest National Park. Making my way toward the north edge, I passed ancient trees transformed into brilliantly hued stone formations and then came face to face with the surreal shifting colors of the Painted Desert.

Roadside attractions heat up on the way to Flagstaff, and it’s hard to miss the signs enticing travelers to “Sleep in a Teepee” at Wigwam Village. The Wigwam Motel in Holbrook is one of the only surviving tee-pee motels on Route 66, mimicking its counterpart in San Bernardino whose sign famously invited guests to “Do it in a Tee-Pee.” The Holbrook property features handmade hickory furniture, a vintage Studebaker automobile, and a museum with Route 66 memorabilia, Indian artifacts and Civil War collectibles. 

Back on the highway, the “Here It Is” series of billboards culminate in a pit stop at the Jack Rabbit Trading Post (look for the creepy giant jackrabbit in the parking lot) where you can pick up a fake tomahawk and “Here It Is” shot glass. In Winslow, stand under the enormous “Girl, my Lord, in a flatbed Ford” mural at the corner of Kinsley and old Highway 66, made famous in the Eagles “Take it Easy” song. And yes, you can pose in front of a red flatbed Ford parked on the curb.

Hotel Monte Vista

It goes without saying that the most significant Route 66 side trip from Flagstaff is the Grand Canyon, America’s cherished natural landmark. After spending an afternoon hiking the south rim of the park, I made my way back to Hotel Monte Vista in downtown Flagstaff, towering in all its storied glory above the downtown historic district just one block off Route 66.

Built in 1927, its overnight guests in the early years included Spencer Tracy, Esther Williams and Barbara Stanwyck as well as Humphrey Bogart while the hotel served as a film location for Casablanca in 1942. The hotel offers access to a system of notorious underground tunnels reportedly constructed by Chinese immigrants and later used as opium dens and gambling parlors.

The Monte Vista Cocktail Lounge became a legendary bootlegging site and the city’s first speakeasy during Prohibition. Ghosts stories abound, including the presence of a bank robber who died in the lounge after being injured in a nearby heist, and a transparent couple laughing and dancing continually for years on end.

Read reviews of the Hotel Monte Vista

Grand Canyon Caverns Inn

Little did I know that a bit further down Route 66 lies an opportunity to sleep in an underground cave 220 feet below the earth’s surface. Just east of Peach Springs, a kitschy big-toothed T-Rex belies the splendor of Grand Canyon Caverns, a natural phenomenon carved out over a period of 65 million years. Tucked beneath (way beneath) the Grand Canyon Caverns Inn in the cave suite that’s completely devoid of light, life forms and noise, making it potentially the oldest and deepest hotel room in the world.

An elevator descends 22 stories underground and deposits you at the 400-foot-long cave room with 70-foot ceilings. But overnight guests claim there’s plenty of company down there; the caves were once a Native American burial site and are said to be haunted by Indian ghosts performing ritual dancing and chanting.

Read reviews of the Grand Canyon Caverns Inn on TripAdvisor

California: The Georgian Hotel and Santa Monica Pier

Crossing the California state line on old Route 66 doesn’t immediately bring a burst of sunshine on a glittering ocean beach. The Mojave Desert gets its say first with a stopover in Newberry Springs for lunch at the Bagdad Café, a filming site for the cult classic film by the same name. I did some quick leg-stretching while roaming the Mother Road Museum in Barstow and the Route 66 Museum in Victorville, both chockful of history and stories.

The ghost town of Calico is worth a 3-mile detour to walk through deserted streets of a once-thriving silver mine town teaming with taverns, brothels and rowdy arcades. Before approaching the last stretch of the Route, I left my mark on the Graffiti Corridor near Chambless, where all travelers are encouraged to contribute personal art representing their journey along the 2,448-mile Main Street of America.

Finally, after a slow crawl through modern-day Los Angeles, the Historic Route 66 comes to an end at the crashing waves of Santa Monica Pier, punctuated by the quiet whirl of the iconic Ferris wheel under sunny Southern California skies. A sign states simply, “End of the Trail.”

A short walk along Ocean Boulevard from the pier, Santa Monica’s “First Lady,” The Georgian hotel crowns the coastline with a genuine symbol of America’s expansion in the 1930s. Like the Mother Road, the storied hotel harbors the moments that define American history.

From its Romanesque Revival and Art Deco architecture to its days as a speakeasy during Prohibition, The Georgian has been a hideaway for both glamorous movie stars and notorious gangsters such as Al Capone and Bugsy Siegel. It also housed aircraft designers and servicemen during World War II and became the summer home for First Mother, Rose Kennedy, in the 1960s.

Read reviews of The Georgian hotel on TripAdvisor

The fact that Pulitzer Prize-winning photographer Dorothea Lange captured her iconic image of the poverty-stricken Migrant Mother in California just three years after The Georgian opened its doors again reflects the complexity of Route 66.

Born in a teepee in Oklahoma Indian Territory and forced to seek work as a farm laborer in California during the Great Depression, the migrant mother Florence Owens Thompson was living in a car with her six children when Lange photographed her on the side of the road. She had just sold the tires on her car to buy food.

Decades later, when finally tracked down and identified by a reporter, Thompson admitted that she never really settled into an ordinary life after her migrant years. Like millions of restless sojourners who still make the westward journey to California, Florence said simply, “I need to have wheels under me.” 

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