9 Must-See Stops on Route 66

Technically, the start of Route 66 can be found in Chicago’s Millennium Park at Buckingham Fountain. But since you’re not going to pull up your Toyota to the edge of the spraying water, start in the quiet suburb of Joliet, Illinois—specifically, the Joliet Area Historical Museum—where you’ll catch an awesome exhibit on the route’s Muffler Men, the iconic advertising fiberglass giants that dotted the route. (Some notable ones are still standing, like Gemini Giant in Wilmington, Illinois.)

In Collinsville, you can get two very diverse Route 66 experiences. You can see the World’s Largest Catsup Bottle, or you can see a UNESCO World Heritage site—or you can see both.

The former is a 70-foot (21-meter) bottle set atop a 100-foot (30-meter) tower. The latter is Cahokia Mounds, the largest pre-Columbian settlement north of Mexico. This very destination was the civil and religious center of the Mississippian Culture. It’s also been declared a National Historic Landmark and is one of 24 UNESCO World Heritage sites located in the US.

Just 15 minutes from Cahokia Mounds, Gateway Arch National Park marks the only national park famous for an artificial creation: the St. Louis Arch. Representing the westward expansion in the US during the Jefferson era, the arch is a sight to see. Take a moment to ride the tram up into the arch, pondering how all this led to so much of this country’s history, from the Dust Bowl to the Trail of Tears to the creation of Route 66.

With more original Route 66 road miles than any other state (and home to those Dust Bowl refugees), the National Route 66 Museum in Elk City takes its job seriously. You’ll get the chance to hop into a 1955 pink Cadillac, listen to the sounds of the Big Band era, or catch an old film at a theater.

If this doesn’t line up with your itinerary, the Oklahoma Route 66 Museum in Clinton—about a half hour away—also offers a taste of the 1950s, including some changing special exhibits. You can even grab a seat at a recreated diner.

Pair that shiny pink Cadillac experience with 10 rusting ones buried nose-down in the dirt. At Cadillac Ranch, west of Amarillo, that’s exactly what you’ll find—only they’ve been spray-painted in a rainbow of colors, vividly contrasting with the beige and brown Texas desert.

Originally, these cars ranged in production years and styles, from the 1949 Club Sedan to the 1963 Sedan de Ville. Though vandals have stripped the bodies of their most stylistic parts, it’s still a unique and interesting site to visit along the route.

Related: 10 of the World’s Best Experiences for Car Lovers

You probably know the lyrics to the famous Eagles song “Take It Easy,” which reference Winslow, Arizona. Winslow is a hotbed of Route 66 history, and even if you didn’t plan to stop there, you’d definitely catch the massive Route 66 sign on the corner of Old Route 66 and North Kinsley Avenue.

The small town is worth a quick visit. Snap a photo here, check out the town’s Route 66 murals and statues, and, if you need a break from driving, grab a sleep at the iconic La Posada Hotel.

Insider tip: If you’re into wild sights and the outdoors, Meteor Crater—the largest in the US—is less than 30 minutes away. It’s more than a mile (1.6 kilometers) wide.

Vintage neon signs, Tex-Mex diners, and retro motels line the main drag of Tucumcari, home to what just might be New Mexico’s most iconic Route 66 stop: the Blue Swallow Motel, still open for business.

Single-stall garages sit next to every room, giving the motel a very Cars-esque vibe. Even if you’re not looking for a spot to hang your head and park your SUV, snap a shot of the iconic sign.

Most towns were made by Route 66 and consequently busted by Route 66, back in the day when many weren’t included on I-40’s route. But not Calico, a mining town in California abandoned on its own in the 1890s.

Route 66ers have helped give this eerie spot new appeal. Today, the town has been restored to look like it did back in its buzzier days. Pan for gold, hit the trails, gawk at the wooden buildings and mining-era structures, stroll the museum and shops, or even book a rustic cabin for a night. It probably won’t be haunted.

Most people will tell you Route 66 ends at the Santa Monica Pier. You should definitely stroll its length, scope out the beach, check out the boardwalk, grab some fresh shrimp, ride the Ferris wheel, or fly on a roller coaster—this pier is hardly your grandpa’s fishing dock.

But once you’ve done all that, know that the actual end of Route 66 is at the corner of 7th and Broadway in downtown Los Angeles. This spot was chosen for its wild claim to fame: With 504,000 people crossing those streets each day in the 1920s, it was the busiest intersection in the world. The intersection remains at the heart of the city’s theatre district, so end your adventure with drinks and a show at a historic venue like Orpheum Theatre.