Where to eat, what to see, and where to stay on a perfect Route 66 road trip.

By Anne Olivia Bauso
August 22, 2020
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Editor’s Note: Travel might be complicated right now, but use our inspirational trip ideas to plan ahead for your next bucket list adventure.

Route 66 doesn’t always surface on Google Maps, but it’s there. The most celebrated stretch of asphalt in America rolls out from the heart of downtown Chicago and begins its epic journey west toward the Pacific. So-called “Mother Road” slides through endless farmland, forgotten towns, and the spectacular desert of the American West. The scenery is a thrill, but it’s the stops and sights along the way — each seemingly more mind-blowing than the last — that make the Route 66 road trip. There’s the infamous 1858 penitentiary from Beat literature and Prison Break. You can tour it the day you set off. A barbed wire museum? Texas has one, complete with the recreation of a diner serving 20-cent pie. A landmark “soda ranch” is the pick-me-up pit stop you didn’t know you needed in the Oklahoma plains. Read on for a state-by-state, Chicago-to-L.A. guide for the ultimate American road trip.

Illinois

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It’s day one: You’re going to need a good breakfast. Fuel up on monster omelets and bottomless coffee at local favorite Lou Mitchell’s (you might just meet fellow Route 66 road-trippers in a neighboring booth). If you want to stretch your legs before the first phase of your journey, Chicago’s Millennium Park is an excellent place to do it. From there, it’s just one block to the Historic Route 66 Begin Sign. Snap a selfie — you’re officially on your way. If you couldn’t bear the wait times for breakfast in Chicago, Dell Rhea’s Chicken Basket is your first stop. The 1930s gas station/lunch counter is now a Route 66 icon for its superlative fried chicken. Look for the restored neon sign — so retro you’ll half-expect to see chrome-stripped Bel Airs parked below it.

Channel Kerouac in “On the Road” and go “by the Joliet pen” — the pen being infamous Old Joliet Prison (also immortalized in “The Blues Brothers” and a particularly harrowing Bob Dylan ballad). Set foot inside the 20-feet-high walls and explore the creepy grounds. Stand up straight — you might reach the knee of the Gemini Giant, a 30-foot Muffler Man statue patrolling the Launching Pad Drive-In, now a gift shop. Swing by historic sites dotting the road, like Ambler’s Texaco Gas Station and Funks Grove Pure Maple Sirup, where you can buy maple candies for the console. For heartier fare, head to Maid-Rite Sandwich Shop in Springfield for beef sandwiches and shakes. If you have it in you, drive on till you see the looming Gateway Arch of St. Louis.

Missouri

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Welcome to St. Louis, the Gateway to the West. Dig into country-fried steak or a stack of pancakes at Southwest Diner before braving a tram to the arch’s peak, touring the 19th-century Anheuser-Busch brewery, or walking high above the Mississippi on famous Chain of Rocks Bridge, whose span jauntily crooks to the north. Drink up the city life; outside of St. Louis, the drive slips through quaint small towns and rolling green hills. Dip into Meramec Caverns, a dramatic cave complex (and alleged Jesse James hideout) with guided tours. Stay the night in a tidy stone-and-mortar cottage at 1930s landmark Wagon Wheel Motel.

The nearby Fanning 66 Outpost is required stopping for many Route 66 veterans. They’re not wrong: The general and farm store has a giant rocking chair for photo ops and popcorn and glass-bottle soda for snack-stocking the car. Veering south of the highway, the Mark Twain National Forest is a lovely place for a picnic; its easy Stone Mill Spring hike has pretty views over Big Piney River. Dial the nostalgia factor to an 11 by catching a double feature at the 66 Drive-In, then crash at Boots Court Motel, complete with period furniture and radios piping out big-band music. The unassuming Joplin History & Mineral Museum is a surprise find, with local discoveries (a wooly mammoth tooth) and delightfully oddball antiques (old circus funhouse mirrors, “Bonnie and Clyde” memorabilia from their Joplin bolthole, and an entire exhibit of cookie cutters).

Oklahoma

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Peek inside the Coleman Theater, a Spanish Revival gem from the vaudeville days, and see the ghost of the abandoned Chelsea Motel. At Totem Pole Park, gaze up at the largest totem pole outside of Alaska and the Pacific Northwest. The roadside whimsy continues at the Blue Whale of Catoosa, an adorable whale whose smiling mouth you can walk right through. The Golden Driller statue was plonked at the entrance of the Tulsa Expo Center in the 1960s, where he stands to this day on concrete work boots the size of cars. Tap into Tulsa’s amazing barbecue scene at Burn Co, a popular spot that grills and smokes its meat in Tulsa-made charcoal ovens, or keep it simple with a patty melt and ice cream float at Rock Cafe, 50 miles to the west. Gearheads and Marvel fans adore Seaba Station Motorcycle Museum, a former gas station now wall to wall with bikes, from a 1909 Triumph to a custom-built ride used in Captain America film shoots. Thirsty? Shelves at the landmark Pops in Arcadia hold sodas — 60-some kinds of ginger ales, more than 130 types of root beers — your taste buds have never dreamed of. Right before the Oklahoma-Texas border, stop by eerie little Texola, with a population of 34. Passersby can still see relics of the old farming town, notably a one-cell cinder-block jail all alone in an overgrown field.

Texas

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The gloriously Art Deco Tower Station and U-Drop Inn Cafe give travelers an old-school Texas welcome. Originally a gas station/diner, the pristine little visitors’ center has classic Conoco pumps and a booth where Elvis once ate. You probably never thought you’d visit a museum dedicated to barbed wire, but here we are — the Devil’s Rope and Route 66 Museum tips its rancher hat to the spiky fencing material, as well as other artifacts from the state’s ranching heritage, like the cattle brand used at Lyndon B. Johnson’s Texas ranch.

A remote Panhandle location doesn’t stop the tiny town of Groom from having its share of bizarre sights. The largest freestanding cross in the U.S. shoots 190 feet in the air here, while the Britten Leaning Water Tower has been grabbing roadsters’ attention for decades. In Amarillo, stroll the city’s antique-shop-filled Route 66 Historic District and kick back at down-home burger joint Coyote Bluff Cafe. Or, if you’re up for a challenge (and the tourists), see if you can put away 72 ounces of steak at The Big Texan. Starlight Canyon, a bed-and-breakfast with cabins and an Old West vibe, is a nice alternative to Amarillo’s endless string of chain motels.

If you miss Cadillac Ranch on your way out of town, did you even drive Route 66? The must-see, kitschy-cool landmark features a group of vintage Caddies buried nose down in the ground, their tail ends poking skyward and covered in graffiti. Celebrate hitting the halfway mark — Chicago is 1,139 miles behind you, L.A. 1,139 miles ahead — with a slice of pie at the throwback Midpoint Cafe.

New Mexico

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In time, the dusty flatlands of the Panhandle give way to the unreal landscape of the American West. Opened the same year (1939) that the “The Wizard of Oz” came out, Blue Swallow Motel is everything Americana lovers could want in a place to stay. Expect attached garages next to each room, Frank Sinatra crooning through outdoor speakers, and arguably the best neon sign outside of Vegas. What began as an artist’s hobby of carving tiny figures has sprouted into the Tinkertown Museum, a rambling warren with detailed Old West dioramas and walls made from concrete and 55,000 glass bottles. Grab a pic in front of the wall of vintage tin signs at 66 Diner, and might as well order a Frito pie and banana split while you’re there. If you’re RV-curious, Enchanted Trails RV Park & Trading Post has 60s-era trailers to sleep in for the night. Traditionalists might continue on to El Rancho Hotel, and stay in a room where John Wayne once slept.

Arizona

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Route 66 cuts through the stunning red mesas and eerie moonscape of the Petrified Forest National Park. The Rainbow Forest Museum is a starting point for hiking trails to the famous petrified logs. Drive to the Blue Mesa trail for a one-mile loop through hilly badlands. The kitsch flag soars at Wigwam Motel, considered an essential stopover by many road-trippers. The 15 guest rooms are modeled after tepees (not wigwams), and the 1950s cars parked outside add to the vibe.

Walk the rim at Meteor Crater Natural Landmark and see the chilling, prehistoric footprint of an asteroid that smashed into Earth. Of course, all desert marvels seem like a warmup in the face of the mind-bogglingly vast Grand Canyon. (Detour 60 miles north at Williams, Arizona, to reach the national park’s South Rim.) Serious planners who book far in advance might score an edge-facing cabin at Bright Angel Lodge, or a spot in Phantom Ranch at the bottom of the canyon. Back on 66, glide through a wide-open expanse of prairie and red rock, checking out time-capsule towns like Seligman, Peach Springs, and Kingman along the way.

California

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The Golden State — the final leg on Route 66’s slow unrolling toward the Pacific. The semi-defunct Roy’s Motel and Cafe, smack dab in the Mojave Desert, is a fun stop en route to Calico Ghost Town. The roadside attraction recreates its California Silver Rush heyday with pioneer-style restaurants, shops, and a narrow-gauge train through the bone-dry terrain. The glass-bottle “forest” Elmer Long's Bottle Tree Ranch is a funky oasis in the dusty wilderness. If you missed the tepee experience at the Wigwam Motel in Arizona, its San Bernardino outpost offers you one more shot.

Not far is the original McDonald’s, now a free museum and quirky shrine to the fast-food giant’s humble midcentury beginnings. The cheery yellow Cucamonga Service Station serves as a tiny Route 66 museum, its mint-condition Richfield pumps from 1915 still advertising 18-cent gallons of gas. Finally, it’s west to the Santa Monica Pier — the all-American boardwalk; a parade of pedestrians, partiers, and performers; and the official end of Route 66.