I’d wager that most people driving the length of Route 66 have researched, planned, and dreamed of it for a long time before their wheels first hit the road. And why not? It’s the ultimate road trip on a road so famous that songs have been written about it.
In October, 2019, my wife Penelope attended a psychology conference in Chicago, and like a dutiful husband, I tagged along with her to the Windy City. We are from Australia and we’d only previously had the big-city experience in the U.S., visiting places like Los Angeles and New York.
We wondered if there was a more interesting way to get back to L.A. from Chicago, other than flying, and the internet’s collective knowledge answered: Route 66. It was an easy decision to make. I ordered a Route 66 guidebook from eBay and also discovered the Roadtrippers app with a great pre-loaded Route 66 trip that we began to customize.
I’d never heard of Tucumcari, Muffler Men, or the Blue Whale of Catoosa. We didn’t know where Albuquerque was, let alone have any idea how many states the Mother Road passed through. Melbourne to Los Angeles is a 14-hour flight, but that’s nothing compared to a cross-country trip along Route 66.
Begin in Chicago
An hour outside of Chicago, our rented maroon RAV4 made the first of its many “essential” stops: Dell Rhea’s Chicken Basket. This icon tops many Route 66 foodie lists thanks to its crispy fried chicken with a tangy buttermilk bite.
Not too far away, in Joliet, is the Old Joliet Prison, featured at the beginning of the 1980s cult film The Blues Brothers, much to my delight. Continuing southwest with tallgrass prairie fields on either side of the road, we were already a far cry from the Chicago skyscrapers.
In Australia we have big things to excite tourists and highlight our heritage, including the Big Banana, the Big Merino, and even the Big Prawn. Suddenly we were here, on Route 66 in Wilmington, Illinois, face to face with The Gemini Giant.
At 30 feet, he stands tall, bathed in the afternoon light along a tree-lined street guarding the renowned Launching Pad restaurant. We learned that these fiberglass giants are called Muffler Men, brought in to advertise to drivers on busy roadsides.
A short while later, we spied the world’s largest painted Route 66 sign in Pontiac, Illinois. Pontiac looked to us like an idyllic American small town with unique stores and a laid-back peacefulness. The Route 66 heritage is proudly embraced here, with a series of murals covering countless walls in the center of town.
With Penny behind the wheel, we were Springfield-bound for our first night and in search of the Pasfield House Inn, a historic bed and breakfast.
In the morning, we felt as though we’d stepped back in time. Tony, our hospitable host, served breakfast with a side of local history and gave us an introduction to the life of Abraham Lincoln. We had no idea that Springfield, Illinois, was where he lived and spent his formative political years.
We toured Lincoln’s house with a National Park Service tour that lasted around an hour. The house is a small, yet stately Greek revival house where Abe lived for 17 years and is beautifully preserved. I’d say we are like most Australians and know little about American history.
An original section of Route 66
Back on the road we managed to find the Auburn Brick Road, a 1.3-mile hand-laid brick section of the original 1927-1940 Route 66 alignment. It has almost been swallowed up by farmland.
In Litchfield, we visited Ariston, which dates back to 1924 and is the oldest restaurant still operating on Route 66—and like us, it has Greek heritage. Next door, Jubelt’s is a bakery from 1922. Surprised to hear Australian accents, the lady that served us put a few extra treats into our bag. I’d never heard of a Bear Claw before, but it quickly became the best tasting dessert named after a bear appendage that I’d ever eaten.
Route 66 continued to ease through farmland and we drove through small communities and saw sights unlike anything in Australia. We got a kick out of the water towers that announce the name of each town that we were in.
The Pink Elephant Antiques market feels like it’s in the middle of absolutely nowhere (Livingston, Illinois) and is a great stop and cool photo-op, with a gigantic pink elephant, a Muffler Man, a Danish-designed Futuro House, and other assorted giants.
It was bright and sunny as we drove into St. Louis, Missouri, where we kept it brief (as we did in all big cities) and admired the Gateway Arch before making our way to the 90-year-old Ted Drewes for a sweet treat. The signature item here is called a “concrete”—a frozen custard so thick that it’s passed to you upside down.
I asked for whatever the most popular concrete was and was duly handed “The Cardinal Sin,” a custard with tart cherries and hot fudge. Places like this reminded us of years gone by and the good times with our families, friends, and endless summer days. I should have bought a t-shirt.
It was nightfall when we arrived in another Springfield, this one in Missouri—the birthplace of Route 66. You can easily sense how proudly Springfield wears its history on its sleeve.
The place to stay in Springfield is the Best Western Route 66 Rail Haven, which dates back to 1938. Here you can stay in an Elvis Room, where The King once stayed, and unsurprisingly it books out well in advance.
Waking up in Springfield
We were the first to sign the guestbook as the Route 66 Springfield Visitor Center opened and we chatted with the locals. All along Route 66, this same morning scene would play out in diners, roadside attractions, and motels. Genuine conversation, consideration for travelers, and an honest experience.
Gary’s Gay Parita was a short drive away and is a classic Route 66 stop. It’s a recreated 1930s Sinclair gas station and features a wealth of petroleum-stained garage-related antiques. But the real experience is a conversation with George.
“If you folks are interested in abandoned things and ghost buildings, make sure you stop by Red Oak II,” he said, giving us rough directions.
This is the unpredictability of a great road trip; one conversation or bit of advice can renew your feeling of adventure as you head off in search of the unknown. You don’t get that on the interstate.
A living ghost town
Red Oak II can be described as an open-air art installation or a living museum created by artist Lowell Davis. It features numerous buildings on an expansive property, which we realized you’re free to walk into and explore. They include a general store, a blacksmith shop, and a vintage Phillips 66 gas station. It may be a ghost town, but everything is immaculately presented.
In Baxter Springs, we stopped by the Kansas Route 66 Visitor Center, which can’t be missed thanks to the restored bright red Phillips pumps. The gentleman who welcomed us with a mono-syllabic grunt and nod gave us leaflets and maps for Oklahoma, a strong handshake, and advice to “stop by the Ku-Ku in Miami, if you’re hungry.”
After crossing into Oklahoma we made it to Waylan’s Ku-Ku Burger, where we found both a lively atmosphere and amazing burgers. Time your visit right and you’ll be greeted by a cacophony of noise as clocks loudly announce each new hour.
With our bellies full, Route 66 took us deeper into Oklahoma. We drove through Afton, Vinita, and Chelsea, along with abandoned motels and remnants of small towns barely standing on the now-quiet Route 66.
But the roads were busier as we reached the outskirts of Tulsa. Leaving the fields behind us, we easily found the amazing Blue Whale of Catoosa, which took the title of quirkiest Route 66 attraction for us. After stopping by Tulsa’s 75-foot, 60-year-old Golden Driller, our appetites led us to the classic El Rancho Grande Mexican restaurant with its great neon sign.
Barely across the Oklahoma-Texas state border is Shamrock, a tiny town where we bunked for the night at the Western Motel. In the morning, we visited the Tower Station and U-Drop Inn (built in 1936), one of the most elegant buildings on Route 66 with its two towers, green glazed ceramic tile walls, and neon light accents.
We were warmly welcomed by two sweet ladies, Hazel and Patsy, who were very interested to meet us and hear our story. We continued to experience nothing but warm hospitality and friendly Americans.
The Big Texan Steak Ranch in Amarillo greeted us at midday as Texas flags fluttered in the stiff wind. This place is what Australians think all of the U.S. is like: loud, proud, and unapologetically American. The sign featuring a 25-foot cowboy has been lighting up the Amarillo sky since 1960.
The midpoint of Route 66
It was following our big lunch that we arrived at the tiny town of Adrian, Texas, population 167, to find the Midpoint Cafe. Here, visitors look for the sign that reads: “Los Angeles 1,139 miles—Chicago 1,139 miles.” We’d arrived at the exact midpoint of Route 66.
Like countless travelers before us, we were thrilled with this milestone and a brief sense of achievement hit us. We celebrated with two of the cafe’s well-known Ugly Crust Pies.
Not too much further along the route we found Glenrio, a ghost town. We learned that it was once a thriving Route 66 stop with diners, motels, and even a dance hall, but today it is utterly deserted.
Penny and I felt a little uneasy and conflicted. We could sense the hopes and dreams that were crushed here. Of all the dead and dying towns we’d seen on Route 66, this one felt the most lifeless.
The atmosphere changed again in the early afternoon when we crossed into the Land of Enchantment and arrived in Tucumcari, New Mexico, a favorite town of many Route 66 roadtrippers.
The Blue Swallow Motel must be the most photographed motel on Route 66, having welcomed travelers since 1939. Across the road is Tee Pee Curios, which today sells decent souvenirs.
Even further into New Mexico we arrived in Gallup. “Charm of yesterday—convenience of tomorrow” was the promise made in blue neon from the towering sign of the El Rancho Hotel and Motel.
It immediately evoked the golden era of Hollywood and immersed us in a familiar Western movie vibe. The grand square lobby was adorned with Navajo rugs, hand-carved wooden furniture, and deer taxidermy, all lit up by enormous stained-glass chandeliers.
By morning, the lobby was a flurry of activity as people readied themselves for their respective adventures. We’d decided to continue the Western vibe and detour off Route 66 three hours north to Monument Valley. But that’s a story for another time.
After our detour, we ascended into Arizona’s Coconino National Forest. The afternoon sun was blocked out by pine trees which left long shadows as Highway 89 hit historic Route 66 and we entered Flagstaff.
Flagstaff is a thriving and charming town at an elevation of 7,000 feet (2,100 meters) and Route 66 was abuzz with activity. Visitors should check out the Lowell Observatory (established in 1894), best known for the 1930 discovery of Pluto.
Williams is 30 minutes further up Route 66 and is another charming town nestled in the pine country of Arizona. Known as the “Gateway to the Grand Canyon,” you can stop by Williams for either the Route 66 experience or use the town as a launching pad to visit Grand Canyon National Park.
A neon steer stood out in the cold night, glowing and humming outside Rod’s Steakhouse where we enjoyed our final Route 66 dinner.
Later we breathed the alpine air deeply and gazed up at the stars. The inky sky was clear and we still had a small drive ahead to make it to Seligman (population 456) for the night. We were quickly running out of Route 66 and we knew it. We wished it would go on and on.
Screaming for attention in Seligman
We stayed at the Aztec Motel because it was the only motel that didn’t have any cars parked outside. We were the only ones there. Marie, the owner, told us that she’s happy when she has even one room booked for the night.
The morning light flooded the cheap, but spotless, motel room earlier than usual. It was 7 a.m. and we had gained an hour somewhere.
Just like the Aztec, all of Seligman seems to survive on Route 66 nostalgia and the colorful main drag was screaming for attention. Each business seemingly tried to out-do its neighbor to attract visitors. It’s tourist kitsch, but we liked it. We learned that this tiny Route 66 town was saved after locals banded together a decade after their town had been bypassed by the new interstate.
Next we visited Kingman and Oatman, where we experienced one of the most scenic sections of the entire route: the Oatman Highway. Nestled in the Black Mountains of Mohave County, there was little room for error on the winding road and its hairpin turns. We took it slow and enjoyed the incredible views.
Oatman itself is a small village and a living ghost town famous for its population of wild burros. In its heyday it was a thriving gold mining town and when the mine was closed during World War II, the burros were set free. Their descendants now come into the tiny town where they’re fed and photographed by tourists.
Driving into California, on our final miles of Route 66, we felt that twinge of sadness you feel when you know something good is coming to an end.
Cutting through the bleak desert skyline appeared probably the most iconic Route 66 roadside sign. Roy’s Motel in Amboy is on a desolate stretch of road, and is a popular sight near the end of the Mother Road.
We talked to a young Polish couple with the road ahead of them heading east. They’d just started their road trip and Roy’s was their first stop. I can’t explain how envious we were.
We passed through Barstow and felt the roads get hectic in San Bernardino. There are original traces of Route 66 between San Bernardino and Los Angeles, and we kept a look out for classic diners, motels, and neon signs. After a week on old Route 66, we had a keen eye.
It was around 11 p.m. as we pulled into our expensive West Hollywood hotel and our road trip came to an end. Flyers, maps, and leaflets were strewn across the back seat. A bellboy took our luggage and another gentleman parked our trusty maroon SUV. At check-in we told the front desk clerk that we’d just driven from Chicago on Route 66. He smiled politely but didn’t really care. We said to ourselves, “Maybe we’ll get to Santa Monica Pier tomorrow.”
(You can read about our full adventure in a lot more detail at roadtrip66.com.)