Route 66 Road Trip: Six Days Along the Historic Route and Where to Stay

A Route 66 road trip is a must for any lover of mid-20th Century Americana. Follow this six-day itinerary complete with hotels and motels along the way.

The sun is setting over the empty highway, turning the view through my car’s windshield into a giant shifting oil painting of bold orange, bright yellow and vibrant pink and purple hues juxtaposed against sagebrush and cacti-strewn desert backdrop. I’m somewhere between Gallup, New Mexico and Winslow, Arizona, road-tripping down Route 66 with one of my best friends.

I roll down the windows and pump the music—”On The Road Again” by Willie Nelson—inhale the fresh, dry air and feel a rush of adrenaline. We’re the only car kicking it down this stretch of the Mother Road. There’s barely a bar of service on my cell phone and no hints of civilization in any direction. There isn’t even any livestock. Just wide-open stretches of nothing. I’m acutely aware that this feels about as remote as it gets on an American highway in the Lower 48 these days.

This feeling is exhilarating.

Running for nearly 2,500 miles from Chicago to LA, Route 66 was officially decommissioned back in 1985 but served as America’s Main Street during its motoring heyday in the 1950s and 60s. Driving the highways and byways that comprise Route 66 is a trip back in time, one that is heavy on the nostalgia and Americana kitsch and still as much a rite of passage today as it was a half-century ago.

Follow this six-day east to west odyssey, complete with hotel recommendations, to find out why.

Start: Chicago


The night before setting off on your Route 66 journey, treat yourself to a luxe hotel experience with a stay at The Langham, Chicago. Just about half a mile from the start of the old Mother Road, The Langham doesn’t specifically have a Route 66 theme but the location is ideal. The hotel is set just back from the Chicago River and a block from shopping and dining on The Magnificent Mile. The five-star hotel also offers elegant rooms and suites boasting city views from large windows that let you get a good night’s rest before your epic road trip.

In the morning, grab breakfast nearby at the landmark Chicago diner Lou Mitchell’s. Serving meals since 1923, it’s the perfect place to fill your stomach before hitting the highway. Right at the start of Route 66, it does oversized fluffy omelettes stuffed with your choice of toppings and thick-cut French Toast among other breakfast choices. There’s often a wait, but there are free doughnut holes to munch on while you do.

After breakfast, take Adams Street for 1.5 miles to Ogden Ave and turn left to follow the route out of downtown Chicago and into the suburb of Cicero.

The Langham, Chicago

Top rated
9.8 Excellent (5448 reviews)

Day 1: Chicago to Springfield, Missouri

Route 66 begins in downtown Chicago on Adams St just west of Michigan Ave. Here, you’ll find the Historic Route 66 “Begin” sign. For travelers coming from the other direction, note that the “End” sign is at the corner of Jackson Boulevard and Michigan Ave.

From Chicago, it’s an eight-hour drive to Springfield, Missouri, which is considered the true birthplace of Route 66. It was here that the meeting designating the Mother Road as such was held in 1926. Head to Park Central Square to catch up on everything Route 66 at the History Museum on the Square.

A Classic 1950s Motoring-Era Motel


Staying in classic 1950s motoring-era motels on your Route 66 road trip is part of the adventure. But, sadly, many of these yesteryear relics have gone downhill over the years and are not visit-worthy. This is not the case with the Best Western Route 66 Rail Haven.

On the National Register of Historic Buildings, it has a classic drive-up motel U-shape set-up. And while the lobby is decorated to take you back to the 1950s, the rooms feature modern upgrades including crisp white duvets rather than the scratchy, polyester comforters often associated with roadside motels. The hotel’s greatest 15 minutes of fame happened in 1956 when Elvis Presley stayed the night and today you can book the Elvis Suite where he slept.

Best Western Route 66 Rail Haven

Top rated
8.8 Excellent (2284 reviews)

Day 2: Springfield to Oklahoma City

Leaving Springfield, Route 66 dips southwest into Oklahoma, which hosts 426 driveable miles of the Mother Road. The term “Mother Road” actually comes from John Steinbeck’s 1939 classic, The Grapes of Wrath, which begins in Dust Bowl-stricken Oklahoma during the Great Depression. The novel follows the journey of the Joad family across the state as they make their way west to California.

Route 66 is also known for its quirky roadside attractions, many of which come in the form of oversized statues in the Midwest. In Foyil, you can pay homage to the world’s largest concrete totem pole. While just outside Catoosa there’s an 80-foot long Blue Whale statue for selfie snaps. And in Arcadia, 90 miles southwest of Tulsa, there’s a 66-foot bottle of soda pop fronting the Pops 66 Soda Ranch, which is an eclectic glass-walled gas station and restaurant.

Inside, you’ll find more than 700 kinds of bottled soda for sale that ranges from normal flavors to the ultra-bizarre (think peanut butter and jelly, buffalo wing, maple bacon, and lemon meringue pie). If you’re craving a juicy burger topped with melted American cheese, a side of onion rings and a thick shake in the flavor of your choice, then head to the onsite diner for a sit-down meal.

A Unique Piece of OKC History


Spend the night in Oklahoma City. It doesn’t host any worthy old motor lodges, but it makes a realistic stopping point driving Route 66 in this direction. The Colcord Hotel may not have Mother Road ties, but you do get a unique piece of OKC history out of the stop. The 12-story hotel constructed in 1911 was OKC’s first skyscraper. Today, the four-star hotel has stylish rooms feature a soothing cream and grey color palette.

Colcord Hotel Oklahoma City, Curio Collection by Hilton

Top rated
Oklahoma City
9.6 Excellent (2160 reviews)

Day 3: Oklahoma City to Tucumcari, New Mexico

Before exiting Oklahoma, make a stop in Clinton, where you’ll find the Oklahoma Route 66 Museum. It uses music and video displays to show you some seven decades of Mother Road history.

Cross the border into the Texas panhandle and grab lunch in the small town of Adrian. The Midpoint Cafe is a 1950s-style diner that marks the halfway point between Chicago and Santa Monica. Order one of the Midpoint Ugly pies, which are a time-honored sweet treat that has even survived ownership changes over the years.

After filling up, continue another 63 miles to the New Mexico line and then on through the stark desert landscape to Tucumcari. The tiny ranching town has long been a favorite Route 66 stopover. After dark, it shines like a beacon of neon brightness from the signs illuminating its kitschy sleeping establishments.

Keeping The Motor Era Alive


One of the neo signs shining the classic Roadrunner Lodge. The owners do a great job of keeping the motoring era alive by going so far as to broadcast a short-range radio program with music and even commercials from the motel’s 1950s and 60s heyday. Come morning, grab a complimentary breakfast at the Kix on 66 diner across the street before motoring on out.

Roadrunner Lodge Motel

Top rated
9.4 Excellent (1044 reviews)

Day 4: Tucumcari to Albuquerque

Heading west across New Mexico towards Albuquerque, stop off in Santa Rosa. The tiny town is famous for its scuba diving. How? In the 81-foot-deep Big Hole, which is the result of a naturally flowing spring dumping 3,000 gallons a minute of water into this cavern. The water is very clear and not super cold (it stays a consistent 64 degrees Fahrenheit all year). Diving here is DIY and you will need to show PADI certification proof and buy a permit to swim.

If diving isn’t your thing, no worries. Santa Rosa is also home to the Route 66 Auto Museum, which has about 35 classic cars on display as well as plenty of Mother Road memorabilia. Afterwards, have lunch at Joseph’s Bar and Grill, where old road trip photos fill the walls. The menu is a mix of American and Mexican family recipes. Order anything smothered in green chile.

A Classic Motor Lodge


It’s 120 miles from Santa Rosa to Albuquerque, your home for the night. Route 66 runs right through the city center as Central Ave and here you will see a neon-lit sign for the retro Monterey Non-Smokers Motel. The classic motor lodge hasn’t changed much about its look since the 1960s, but despite the vintage mirrors, wallpaper and bedspreads, the beds themselves are updated and comfy.

The Monterey Motel

Top rated
8.6 Excellent (522 reviews)

Day 5: Albuquerque to Winslow, Arizona

Route 66 follows I-40 from Albuquerque and heads west on the highway for 90 miles to Gallup, where it dips off the interstate to become the town’s main drag. Drive through the historic district with around 20 renovated light-red sandstone buildings, including the El Morro Theater, which was completed in 1926, the same year as the highway. It’s a grand old Spanish Colonial-style affair that still shows movies on Saturdays.

The Petrified Forest National Park is well worth a short detour from the highway—look for the turnoff at mile marker 311, just after crossing the border from New Mexico. It’s one of the most bizarre natural attractions around and is filled with fragmented, fossilized logs dating back 225 million years. Some of the logs are up to six feet in diameter and the way they have been scattered by time in odd formations is equally interesting to see. If you can time it right, this is a fabulous place to watch the sunset.

Back on the highway, it’s just under an hour’s drive to Winslow. The Eagles’ 1972 tune “Take It Easy” memorialized this tiny town, which is also tonight’s stopping point. Snap a photo for the Gram in front of the life-sized bronze statue of a hitchhiker that’s backed by a trompe l’oeil mural of the girl in the flatbed ford from the song.

A Hacienda-style Property


Spend the night at La Posada Hotel. Designed in the 1930s by Mary Colter, the hacienda-style property boasts elaborate tile work, glass-and-tin chandeliers, and Navajo rugs.

La Posada Hotel

Top rated
9.6 Excellent (2185 reviews)

Day 6: Winslow to Santa Monica, California

Leaving Winslow, the Mother Road takes you to the low-key mountain town of Flagstaff that is also home to Northern Arizona University and then to the tiny town of Seligman. Grab a bite here at the Snow-Cap Drive-In, which has been a Route 66 institution since it opened in 1953.

From Seligman, America’s Main Street heads northwest away from the interstate and into the rugged Black Mountains before twisting and turning for another 30 miles past cacti and tumbleweeds into the old mining town of Oatman. Reinvented as a movie set and Wild West town after Route 66 was rerouted around it in the 1950s, today it’s a touristy but fun pause.

Oatman is just 25 miles from the California border where Route 66 heads north from Needles through the Mojave Desert. From here, expects hours of barren empty nothing landscape—it kind of looks like the surface of the moon—until you reach Barstow, which Hunter S. Thompson immortalized with a quote in Fear and Loathing in Las Vegas. The town is also home to the Route 66 Mother Road Museum, which is filled with vintage photos and signs plus a classic car collection.

Route 66 officially ends at the Santa Monica Pier. Getting here delivers a deserved Hollywood-style ending for such an epic road trip with the Mother Road’s original designated route taking you down Sunset Blvd to Santa Monica Blvd. Park at the pier and run into the Pacific Ocean. You’ve earned it.

Finish in a Classy Hotel


You’ve also earned a night’s rest in a classy hotel. Head to The Georgian Hotel, which is a Santa Monica institution right on Ocean Avenue by the pier. The Art Deco hotel was built in 1933, so fits into our historical trip theme, and has hosted the likes of everyone from Clark Gable to Bugsy Siegel over the years. It makes for a great place to toast the end of this epic road trip. Head to the Veranda Restaurant fronting the Pacific Ocean to do so with glasses of bubbly.

The Georgian Hotel

Top rated
Santa Monica
9.1 Excellent (569 reviews)

Feature image courtesy of the New Mexico Tourism Department