Illinois

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 the infamous Old Joliet Prison (also immortalized in “The Blues Brothers” and a particularly harrowing Bob Dylan ballad). Set foot inside the 25-foot-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 restaurant and 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 the 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

Welcome to St. Louis, the Gateway to the West. Dig into a 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 the famous Chain of Rocks Bridge, whose span jauntily crooks to the north. Drink up the city life while you can; 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 the 1930s landmark Wagon Wheel Motel.

Oklahoma

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 world’s largest concrete totem pole. 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 Tulsa’s Expo Square 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 in Jenks that grills and smokes its meat in Tulsa-made charcoal ovens, or keep it simple with a patty melt and ice cream float from the Rock Cafe, 50 miles to the west in Stroud. Gearheads and Marvel fans adore Seaba Station Motorcycle Museum, a former gas station now filled from wall to wall with bikes ranging from a 1909 Triumph to a custom-built ride used in Captain America film shoots. Thirsty? Shelves at the landmark Pops in Arcadia hold classic candies and drinks — over 500 varieties of sodas, ginger ales, and root beers — your taste buds have never dreamed of. Right before the Oklahoma-Texas border, stop by eerie little Texola, with a population of 6. Passersby can still see relics of the former farming town, notably a one-cell cinder-block jail all alone in an overgrown field.

Texas

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 is home to 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 former President Lyndon B. Johnson’s Texas ranch.

Being situated in 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 Steak Ranch. 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. is 1,139 miles ahead — with a slice of pie at the throwback Midpoint Cafe.

New Mexico

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 Las 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 50,000 glass bottles. Grab a pic in front of the wall of vintage tin signs at 66 Diner in Albuquerque, and you 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, although traditionalists might continue to El Rancho Hotel and stay in a room where John Wayne once slept.

Arizona

Route 66 cuts through the stunning red mesas and the eerie moonscape of 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 here are modeled after teepees (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 might score an edge-facing cabin at Bright Angel Lodge & Cabins or a spot in Phantom Ranch at the bottom of the canyon. Back on Route 66, glide through a wide-open expanse of prairie and red rock, checking out time-capsule towns such as Seligman, Peach Springs, and Kingman along the way.

California

The Golden State is the final leg on Route 66’s slow unrolling march toward the Pacific. The semi-defunct Roy’s Motel and Cafe, located smack dab in the middle of the Mojave Desert, is a fun stop en route to Calico Ghost Town Regional Park. 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’s Bottle Tree Ranch is a funky oasis in the dusty wilderness. If you missed the teepee 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 mid-century 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 Santa Monica Pier — the all-American boardwalk with its endless parade of pedestrians, partiers, and performers — and the official end of Route 66.