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

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.

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.

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.

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.

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.

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.