2 Week Route 66 Road Trip Guide

When singer Bobby Troupe wrote the song “Route 66” back in 1946, chances are he had no idea he’d be inspiring generations of bucket-listers to hit the road. Lyrics directing you to drive “From Chicago to L.A./ More than two thousand miles all the way” are better than any map. 

Route 66 was replaced by an interstate highway in 1984, but you can still drive on sections of the original road for almost the entire journey. Along the way you pass weird tourist attractions, abandoned towns that went bust when travelers stopped coming, and some of the country’s most beautiful scenery.  


Get your camera ready, because on the northwestern corner of Adams Street and Michigan Avenue in Downtown Chicago are two signs: the top one reads “Historic Route 66,” and the one below simply says “Begin.” You’ll be itching to begin your journey, but spend the night in Chicago so you have plenty of time to visit the unmissable sights, including the Art Institute of Chicago and Millennium Park, home of the Cloud Gate, which most closely resembles an enormous silver bean. 


It’s 4½ hours from Chicago to St. Louis, Missouri, but a great place to break up the journey is Pontiac, Illinois. Here you’ll find the Route 66 Hall of Fame and Museum, one of many dedicated to the Mother Highway. Don’t forget to head around back for the massive mural featuring a Route 66 marker—your second photo op. 

Stop for lunch at Springfield’s Cozy Dog Drive-In, which claims to have invented the corn dog, then head south past the historic Chain of Rocks Bridge to St. Louis. 

It’s worth a detour here to see the Gateway Arch—travelers along Route 66 certainly did when this engineering marvel opened in 1965. Dinner is at a burger joint locals love—Carl’s Drive-In—followed by a “concrete” milkshake from the walk-up window at Ted Drewes Frozen Custard. Spend a glamorous night at St. Louis Union Station Hotel.  


On your way out of St. Louis, stop by Route 66 State Park, where the visitor center is in a former lodging called the Bridgehead Inn. Nearby is the now closed Route 66 Bridge, which once shuttled travelers across the Meramec River. A short drive south you’ll find the Meramec Caverns, one of the largest cave systems in the world. 

Halfway to Joplin is Springfield, Missouri, known as the “Birthplace of Route 66” because the first stretch of roadway was here. (There’s a sign at Springfield’s Park Central Square, your third photo op.) In a nearby Victorian-era storefront is the city’s oldest tavern, Linberg’s. The dining room, with gorgeous woodwork and a pressed-tin ceiling, is a good spot for lunch. 

The Mother Road used to run straight through Joplin, and locals celebrate this fact at Route 66 Mural Park. When you’re ready for a dinner break, head to nearby Carthage for a burger at Whisler’s Drive Up. (Just remember that it closes on the early side.) If you’re looking for after-dark entertainment, you can’t beat the Route 66 Drive-In, which opened for business in 1949.


Your next step along the journey is Kansas, although Route 66 barely grazes the southeast corner of the Sunflower State. Before you know it you’ll be in Oklahoma, which has the longest drivable stretch of the original Route 66. A great spot to stretch your legs along the way is the enormous Blue Whale, a roadside in the community of Catoosa. 

You’ll know you’ve reached Tulsa when you catch sight of the Golden Driller, dedicated to workers in the region’s oil industry. This is definitely the place for a blast-from-the-past lunch. Our favorites include Ike’s Chili (a modest place that’s been in business more than a century), Tally’s Café (the chicken sandwich has won numerous awards), and Waylan’s Ku-Ku Burger (the last outpost of a cuckoo clock–themed eatery that used to spread across the Midwest). 

Depending on the year, Route 66 followed several different roads through Oklahoma City. The city is built on top of the oil fields, and there are even derricks on the grounds of the Oklahoma State Capitol. Dinner should be at the glitzy Cheever’s, recognizable from its slightly confusing neon sign reading “Flowers.” For generations, the historic building held a family-owned flower shop. If there’s a concert at the iconic Tower Theater, that’s where you want to spend the evening.  


Heading west, you can learn all about the Mother Road at the Oklahoma Route 66 Museum in Clinton. You can’t miss it, as it has some of the flashiest neon anywhere in these parts. (If you do, it’s a half-hour drive to Elk City’s National Route 66 Museum.)

Crossing into Texas—just 179 miles of the panhandle—you’ll encounter some interesting diversions, such as the Devil’s Rope Museum, which pays homage to barbed wire. Take our word for it and order the tasty fried catfish down the road at the Red River Steak House. 

Amarillo has one real attraction, a world-famous art installation called Cadillac Ranch. These 10 classic cars buried fender first in the prairie are worth a little detour. Then it’s off to dinner at the Big Texan Steak Ranch, where anyone finishing a 72-ounce slab of beef gets a free meal. (Aren’t you glad you didn’t fill up back in McLean?)  


Today is one of the longest drives on this itinerary, but the desert scenery is stunning. For a late breakfast or early lunch, stop in Adrian at the Midpoint Café, more or less the halfway point of this journey. Crossing the border into New Mexico, Tucumcari has a string of beautiful neon signs in front of classic motor lodges. The best is the swooping bird atop the Blue Swallow Motel. 

In the early days, Route 66 took a sharp detour north, looping around Santa Fe before heading south again. It’s worth the detour to take in this smart, sophisticated city in the desert. Don’t miss the Georgia O’Keeffe Museum, dedicated to one of the 20th century’s most famous painters. It’s a short stroll from leafy Santa Fe Plaza, where you’ll find award-winning restaurants in every direction. Treat yourself at upscale Sazón. Stay the night at La Fonda on the Plaza. 

Better yet, stay three nights, because there’s plenty to see in and around Santa Fe. Meander along the streets around Santa Fe Plaza, ducking into any of the dozens of art galleries. Take in the 17th-century adobe abodes along De Vargas Street. 

Marvel at the majesty of the San Miguel Mission or the charm of Loretto Chapel. Reserve ahead for dinner at La Plazuela in Santa Fe. 

The next morning—or afternoon, if you’re so enchanted by Santa Fe that you find it difficult to leave—head south to Albuquerque for lunch at 66 Café, a diner that started out life as a Phillips 66 gas station. You can get the lay of the land from the top of the Sandia Mountains with the help of the Sandia Peak Tramway.

Set off into the desert at Petroglyph National Monument, where indigenous people carved patterns into the stone hundreds of years ago. Dine at Mac’s La Sierra Family Restaurant, which has been serving Southwestern favorites since 1952. 

Overnight at the adobe-style El Vado Motel, a Route 66 classic dating from 1937. The next day head west to Gallup. The most unusual attraction here is the tiny Navajo Code Talkers Museum, honoring Navajo speakers who created a simple but unbreakable code used for communications during World War II. The historic El Rancho, dating from 1937, is a popular spot for dining and dreaming. 


Cross the border to Arizona, whose towns are name-checked more often than any other state in the song. On your way to Flagstaff, take a hike past perfectly pre-served trees at Petrified Forest National Park, visible on both sides of the highway. 

Actually, you can forget Winona, even though the song urges you otherwise. Head straight to Flagstaff, where there’s a historic downtown where you just have to take a stroll and perhaps stop for lunch at the century-old Weatherford Hotel. 

With three bars, it’s a bit too noisy for an overnight stay. For that, we suggest driving 30 miles west to the quieter town of Williams, where you can stay at a classic motel like the Lodge on Route 55. Dinner is at another longtime favorite, Rod’s Steak House. 

There’s so much to see in the area that you should budget three nights in the Williams area. First and foremost is the Grand Canyon, an hour’s drive north. Plan ahead and you can score a room at one of the lodges inside the national park. If you’re a mountain biker, Kaibab National Forest is a must. Crumbling parts of Route 66 have been incorporated into trails like Devil Dog Loop. 


Heading west, stop for a bite in Seligman at Delgadillo’s Snow Cap Drive-In. Exit off the highway here, as there’s a 90-mile segment of Old Route 66 between Seligman and Barstow that really gives you the flavor of the open road. Kingman has a strip of historic buildings along its main street, including the now-defunct Beale Hotel. Lunch family-style at Rutherford’s 66 Family Diner. 

Overnight in Kingston, or make your way through the tourist trap of Oatman (where the streets are full of burros looking for a handout) and on to the Arizona-California border, where you can choose from several lodgings on the Colorado River.  


Crossing into California, Barstow is the gateway to Joshua Tree National Park. It’s worth budgeting a day at this otherworldly landscape, especially if your jam is hiking or rock climbing. Stay in Twentynine Palms or one of the other communities near the entrance. 

Barstow itself is home to the jam-packed Route 66 Mother Road Museum, where almost none of the “treasures” on exhibit are labeled. Stop in Barstow for some delicious Mexican food at Rosita’s, or head to Amapola Rico Taco in San Bernardino. For one last taste of Route 66 kitsch, stay at the Wigwam Motel, where 20 concrete teepees make for surprisingly roomy accommodations.  

DAY 14: “.. TO L.A.” 

San Bernardino is the edge of the suburbs of L.A., so from here on out the road is extremely well traveled. Head through the center of this crowded city to Santa Monica Pier, where you’ll find the sign marking the end of the road. It’s your last photo op of the journey, and it’s a beauty.

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