As I’m riding out of Seligman, Arizona, the world begins to change. The landscape opens, revealing barren desert in every direction. A cargo train runs parallel, to my left, while the imposing Aubrey Cliffs line the horizon to my right. The thunderous rumble of the Triumph motorcycle is my soundtrack, while the yellow lines of the road blur into one beside me. Ahead, the gray tarmac rolls on forever. This is the American road. This is Route 66.
I’m here on a personal odyssey: to ride a motorcycle along the entirety of Route 66, from Chicago to Los Angeles. This year marks the road’s 100th anniversary. With businesses, motels, bars, and restaurants all gearing up for the centenary, now is the time. I check into the Kimpton Gray Hotel in the Chicago Loop, pick up the bike — a Triumph Bonneville Speedmaster — and strap down my bags. Just over 2,400 miles separate me from the Pacific. It’s my first solo motorcycle trip, and I feel that thrill of the unknown that you just don’t get on a beach break. Spoiler: I won’t be disappointed.
The idea for a national highway network began in the 1920s. Until then, cars were very simple but difficult-to-drive, open-air machines. The ’20s saw them become mass-produced, cheaper, and modern. With increased adoption by a demographic excited about this technology, and the future of personal travel secured, America needed the road network to better connect the country.
One of the key pipelines was Route 66, the brainchild of Cyrus Avery, a businessman from Tulsa, Oklahoma, who recognized the need for improved infrastructure while also anticipating the financial opportunity in opening up the Midwest. The road was commissioned on November 11, 1926, and Avery’s instinct was to push for the ‘66’ moniker to make it easier to promote. He wasn’t wrong. One hundred years later, Route 66 has almost become a brand, with both Americans and international tourists drawn to its history and what it represents. It’s estimated that up to three million people travel portions of it annually, while around 40,000 complete the full route each year. In a National Park Service study on Route 66’s economic impact, it was found that visitors to the road over the course of one year came from all 50 US states and approximately 40 foreign countries, with the UK, France, and Germany making up the largest numbers.
Route 66’s familiar shield sign is synonymous with freedom and exploration. These days it’s as much a cultural reference point as it is a stretch of tarmac. But it also represents a very specific kind of Americana. The birth of Route 66 coincided with the rise of motels, modern filling stations, diners, and roadside attractions. In today’s digital world, it’s this nostalgia and desire for a simpler time that adds to its allure.
Chicago was the route’s original starting point thanks to its role as the commercial hub of the Midwest during the 1920s, and this still makes sense, with architecture, history, and exceptional food to sustain you before you set off. If you like a sandwich, you eat well here. Lu Lu’s Hot Dogs is a favorite, its ‘combo’ filled with Italian beef, green chilies, provolone cheese, and a Polish sausage, all submerged in a meaty jus; while Lou Mitchell’s is the unofficial kick-off point, a classic diner that’s been in operation since 1923, before the road opened.
These calories are needed for the first day’s ride. I pick up my Triumph from Motoworks, a huge, multi-brand dealer in a converted warehouse. Many will rent bikes, but it’s not uncommon for people to purchase one before starting the route, riding it home or shipping it back.
My first stop is St Louis, Missouri, 300 miles southeast. My bike is a relaxed cruiser with Triumph’s trusty 1,200 cc parallel twin. Forward controls make all-day riding much more tolerable, with your legs extended out in front of you. The soft seat has you sinking into the bike like it’s a favorite armchair. The Bonneville Speedmaster’s low-slung silhouette suits the streets of downtown Chicago, with that bassy engine note reverberating off the surrounding skyscrapers. It channels the mid-century style of vintage Triumphs into a new, more muscular package, perfect for a cross-country jaunt.
And it’s different. The most common bikes you’ll see along the way are the Harley-Davidson Street Glide and Road Glide, two mammoth cruisers with large front fairings and integrated panniers. Acceptable options both, but the Triumph is cooler and rarer. What it loses in outright touring capability it makes up for in style points, and for someone who places a disproportionate emphasis on aesthetics, this is enough for me.
Leaving the city, one of the realities of riding Route 66 soon becomes clear. It isn’t one unbroken road from east to west anymore, and I have to work hard to stay on track, taking numerous wrong turns before connecting back up, only to lose it again. It makes sense to download the Route 66 app, which has the entire journey mapped out for use offline, rather than using traditional navigation apps, which prioritize the Interstate.
The first day also hints at another challenge of riding a motorcycle across a continent: the weather. The day before my departure had been a balmy 82 Fahrenheit, but an overnight tornado saw the temperature drop to 53. Add the wind chill factor and it feels lower still. Two hours into the seven-hour ride, my legs are shivering against the tank. Having forgotten to charge my phone (and primary navigation tool), it subsequently dies just as the bike’s service light comes on. I later discover that this is not a mechanical issue but simply a normal warning that the bike is due its first service, but that discovery comes after a brief roadside meltdown. Freezing somewhere in rural Illinois, I climb into my thermals so quickly that I put a hole through the leg.
Ignoring the cold, I admire two charming filling stations that have been restored to their former glory. The first is Ambler’s Texaco Gas Station in Dwight, Illinois, the longest operating station on the route, having dispensed fuel from 1933 to 1999. The second, the Standard Oil Gasoline Station, 10 minutes down the road in Odell, was built a year earlier, in 1932. Both are great examples of the humble, house-like structures of filling stations of the era.
There are numerous restored attractions along the way. Some have been bought by locals with support of the Route 66 Association, and others by individuals with a passion for history. One such is the Rockwood Motor Court, in Springfield, Missouri. Originally built in 1929, it’s the oldest of its kind on the 66. Distinctive thanks to its ‘giraffe-style’ stone — typical of the Ozarks region — and its neon sign, it was restored in 2019 by Phyllis Ferguson and her husband, who kept everything as original as possible and even live in the main house, as intended by the original builders. “I like to sit in the front room and drink tea while watching the travelers pack up and leave in the morning,” she tells me.
I roll out the following morning, easing into the ride, which takes in Kansas on the way to Tulsa, Oklahoma. Route 66 only passes through Kansas for 15 miles, but the state has made a great effort to embrace it, with its small towns tapping into the heritage. Two, Galena and Baxter Springs, inspired the Disney/Pixar movie Cars. There is a restored filling station, Gearhead Curios, in the former. Its inventive owner created an automotive-themed toilet built from old car parts, fabricating everything himself. I’m told a couple got married in there, and another renewed their vows by the urinal.
It’s these stops that make Route 66 so special. From a life-sized whale model in Catoosa to the many towering ‘muffler men’ — giant 1960s fiberglass statues originally used to advertise auto repair shops and diners — found along the way, there are numerous wild and wacky sites to enjoy. Many of them are original, designed to draw in motorists in the 1940s and ’50s. Unlike many road trips, in which motorists seek out ultimate driving heaven in the form of twisting alpine passes and sweeping mountain views, Route 66 is as much about what you see beside the road. It’s a moving, living, and breathing museum, with a passionate community of people keeping it all going.
One such character is Harley, owner of Sandhills Curiosity Shop in Erick, Oklahoma. His ‘shop’ doesn’t actually sell anything; rather, it acts as a museum dedicated to Americana and roadside paraphernalia. He shows me the oldest 66 sign in Oklahoma, before unsheathing the ‘world’s largest pocketknife.’ As I look around, he starts playing on his electric guitar, the slow melody filling the dark, smoky room. He makes me hold the sign while he takes a picture. “This guy’s riding solo looking for Route 66 chicks,” he says. “He’s probably already had two or three. He’s probably had more than me!” I head out and begin to load up the bike. He comes out, shouts ‘yee-haw’ and slaps the bell above the front door.
Onward to Amarillo, Texas and a stay in the Barfield Hotel, an imposing 1927 skyscraper built by pioneer businesswoman Melissa Dora Oliver-Eakle. Nearly halfway along Route 66, Amarillo is a great place to relax for a couple of days, mid-trip. There’s Bill’s Backyard Classics, a museum showcasing iconic American vehicles once owned by entrepreneur Bill Pratt. The collection includes more than 90 cars, from 1930s Buick hot rods to a 1945 military Jeep and a ’67 Pontiac GTO.
The guide, Gary Rodgers, recounts stories of the road in the 1970s. “I first hitchhiked it both ways from Chicago to Venice, California in 1971,” he tells me. “I was 17 at the time, a true hippy. I got picked up by a van-load of girls one time in Flagstaff, Arizona. I stayed in a commune with them for a couple of weeks. I didn’t have any money — sometimes I went with not one penny — but people always fed me, and I could always get a job because I had skills. It was just an adventure.” I don’t doubt him.
Roadside Encounters
Art Torres, actor in Bagdad Cafe sitting in the eponymous cafe.
Karla Claus, Miss Centennial Route 66 Princess and tour guide.
Harley Russell, owner of Sandhills Curiosity Shop.
Gary Rodgers, guide at Bill’s Backyard Classics.
Elsewhere in Amarillo there’s 6th Street (which is on Route 66), a historic road with antique shops and restaurants. In the evening, head to GoldenLight Cafe, a roadhouse established in 1946; have a green chili cheeseburger and a cold beer, and breathe. There’s no doubting this is a ride of immense solitude. At first, this was challenging. Having left Chicago, a metropolis full of people, with a bar, restaurant, or museum on every corner, I find myself within a few hours in the middle of Illinois, miles from anyone I know and 12 days from my destination.
But despair soon grows into calm. The familiar morning routine of loading the bike, filling up with gas, and setting off to somewhere new is exciting. And the relaxing hum of the machine at 3,500 rpm, floating through small towns, clocking up the miles and making progress, becomes therapeutic.
Riding in a group can be fun, but going solo is liberating. There are no expectations and nobody to impress. Having somewhere I need to end up each day focuses my mind, becoming a singular goal. The days are simple and meditative, the bills, emails, and worries of home forgotten. It’s just me, my iron horse, and the road.
There’s plenty to see in the second section of the trip. The Cadillac Ranch, home to a row of limos buried nose-first in the desert, is just outside Amarillo, while the Midpoint Cafe is the official halfway point of Route 66. Further along are the motel signs of Tucumcari and the roadside architecture of Seligman, but most impressive is the way the landscape changes as you move through New Mexico into Arizona, and then California.
Until now, things have been flat, through the green farmland of Illinois and Oklahoma, and the open plains of the Texas Panhandle. Head deeper into New Mexico and it gets dustier as the desert opens up, with the sandstone mesas of Laguna Pueblo and the red rock mountains of Gallup. You start to see the three-mile-long cargo trains that run parallel to the route, their horns booming as they carve through the landscape alongside you. It changes again in Flagstaff, where the mountain city’s Ponderosa pines and 7,000-ft elevation provide a cool escape from the Arizona heat, as well as a pleasing forest scent as I roll through.
While many choose to drive Route 66, I believe it is best experienced on two wheels. In riding a motorcycle, I’m not just viewing the world from behind a glass screen, I’m part of it. Exposed to the elements, I can feel the subtle temperature changes and smell the burgers frying as I pass another diner. As a solo traveler, I gain the respect of locals who can’t quite believe I began my trip in Chicago, traveling with only three bags strapped down over my rear wheel. Once I hit the West, it’s impossible not to marvel at the cinema of it all. You ride the same long, arrow-straight roads you’ve seen on screen, those familiar mountain backdrops making you feel small and insignificant.
It doesn’t matter if you’re a Euro solo rider, an Upper East Sider seeking solitude, or a group of retirees from the coast, the impact of it all is undeniable. Pull up to your motel for the night, the Americana Motor Hotel in Flagstaff or Tin Can Alley in Kingman, and soak it in.
Descending out of Flagstaff, the desert returns — and it doesn’t leave until I hit Los Angeles. When I do, I fight the traffic and reach the ‘end of the trail’ sign on Santa Monica Pier. It’s a world away from the many small towns found along the route. I find myself missing the dramatic western landscapes and the romance of the open road. I remember the motels and historic diners, and the locals who saluted me on my way. The sun is setting over the Pacific, marking the end of another day in paradise. But it’s only just rising on Route 66 as it celebrates its anniversary, promising the same adventure that’s been its calling card for 100 years. It’s a simple recipe: long roads, wild scenery, and something new on every horizon. And it doesn’t get old.
For more information go to visittheusa.com; flights to Chicago and returning from Los Angeles are available with americansky.co.uk
