Route 66 is the quintessential embodiment of the road and all its greatest promises: freedom and serendipity, kitsch and living history, and a case study of the very particular way Americans have moved and multiplied. You can certainly travel eastward on Route 66 (in fact, we highly recommend it), but there’s no denying the symbolic strength of at least one westward journey along its patchwork of asphalt.
Ready to get started? Don’t leave home without your trusty Route 66 map. It’s a good idea to bring a paper map of Route 66 as back-up in case you don’t have cell reception. But the trip planner is going to be your best friend along the journey, with pre-made maps and guides ready to help make your trip a success.
Here’s some of our favorite Route 66 attractions. Make sure you don’t miss them on your next trip down the Mother Road.
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Gateway Arch National Park is so much more than just the iconic arch. There’s also a free museum with exhibits detailing America’s westward expansion and the building of the Gateway Arch, which is a good place to start if you’re waiting for your ride to the top (or if you’re scared of heights but still want the arch experience). A trip to the top of the Eero Saarinen-designed monument—the world’s tallest arch and the tallest man-made monument in the U.S.—offers great views of both sides of the Mississippi.
The Blue Whale of Cartoosa is one of the most popular roadside attractions along Route 66. It was built by Hugh Davis in the early 1970s as a surprise anniversary gift for his wife Zelta, who loved whales and collected whale figurines. Take time to wander around the remnants of this famed roadside wonder, and have a snack at one of the picnic tables.
Ten Cadillacs stand along Interstate 40, buried in the dirt at the same angles as the Great Pyramids of Giza. Visitors are encouraged to bring a can of spray paint and add their own mark to this unique roadside art installation. Spray painting the Cadillacs is a rite of passage for any true roadtripper, and the installation has gone through quite a few makeovers throughout the years.
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You’d be hard-pressed to find a ghost town more real—or more alive—than Oatman. Located at the edge of Arizona on Route 66 and perched 2, 700 feet above sea level in the Black Mountains, Oatman is a strange place run by wild burros.
Whether you call it the starting or ending point of the Mother Road, the Santa Monica Pier is the perfect spot to stretch your legs or snap photos of the ocean before embarking on a 2, 000-mile trip east. Sure it’s touristy, but that shouldn’t stop you from taking a ride on the 1922 carousel or grabbing something sweet from the soda fountain. From the roller coaster and Ferris wheel to the arcade and the sign noting that it is the official end of Route 66, there’s tons of fun to be had here.
Although it only existed as a unified, legally codified road for 59 years—between 1926 and 1985—Route 66 became a great symbolic trailway of human civilization. It will live forever as a route whose traffic reshaped the world of its time, transporting generations of adventurers, migrants, grifters, and dreamers toward untold opportunities.
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Route 66 gave rise to new towns, new industries, and a new vernacular architecture. A great deal of it was lost when most cross-country travel migrated to the interstates, but today, a thriving community of people who live along the road—travelers, well-wishers, and preservationists—share news and stories, raise money to protect landmarks, maintain museums, and otherwise work hard to protect its legacy. The route’s future, thanks to like you, looks bright.
Although it only existed as a unified, legally codified road for 59 years—between 1926 and 1985—Route 66 became a great symbolic trailway of human civilization.
The Mother Road has been firmly embedded in the American mythos for decades. In the 1940s, Bob Troup pounded out “(Get Your Kicks On) Route 66, ” a catchy and enduring standard that has been covered by dozens of artists, from Nat King Cole to The Cramps. In the 1960s, CBS notched a major hit with Route 66, a series whose plot mostly amounted to two handsome guys rambling around the country in a Corvette roadster. Very few of the show’s episodes were actually set in towns anywhere near the road it was named for, making it clear that Route 66 had already become shorthand for the adventuresome American spirit, and for the open road itself. And since the Mother Road disappeared from official maps and its signage was removed in 1985, its mystique has only grown.
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Use this guide for either westbound (Chicago to Santa Monica) or eastbound (Santa Monica to Chicago) travel along Route 66. For simplicity, this page is organized from east to west, as that’s the most popular way to experience the route. Should you venture from California to Illinois, just start by reading the section on California and work your way up the page.
Chicago, Illinois, is the eastern terminus of the Mother Road—depending on which way you travel, you will either start or end your trip across from Grant Park and Lake Michigan. After leaving the Windy City, the road takes you southwest through rural Midwestern towns full of classic motel neon, vintage filling stations, roadside giants, and historic bridges until you hit the Mississippi River and East St. Louis.
The stretch of Route 66 from Chicago to St. Louis is home to aluminum-and-chrome diners, historic, family-owned cafes, bizarre attractions, and other reminders of the route’s charming past. You’ll also see plenty of cornfields and flat prairie land between the bustling cities and sleepy towns along this first leg.
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There are nearly 300 miles of Route 66 in Illinois. The state is also home to many of the country’s most famous Muffler Men, those fiberglass titans of retro roadside kitsch. A lot of the old route has been gobbled up by modern highways, in particular I-55, but there’s still plenty of neon, fiberglass, and chrome to keep any roadtripper happy. Traditionally, travelers begin their journey southwest near the shores of Lake Michigan, not spending too much time in Chicago. After all, the Mother Road is calling.
Many miles of Missouri’s Route 66 have been replaced over the years by larger highways, so what remains of the original road is a patchwork, especially in and around St. Louis. The Show-Me State contains several abandoned stretches of the Mother Road, but it’s still possible to travel on quite a bit of the original route. More than 300 miles of road takes you southwest from St. Louis to Joplin, a stretch packed with fantastic diners, classic roadside attractions, and classic photo ops.
Few cities are lucky enough to have an architectural icon like the Gateway Arch overlooking the mighty Mississippi River, but there’s so much more to St. Louis. The city has a booming craft brewery scene, a rich history, and top-notch cultural institutions. Whether you’re eating at an old-school soda fountain or getting lost in a phantasmagorical wonderland, St. Louis is an excellent weekend destination.
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The stretch of Route 66 from St. Louis to Tulsa is considered by some travelers to be the heart of Route 66. It’s where east meets west, linking up the Midwest with the West Coast. Much of this stretch is on I-44, which means lots of exits and county roads, but the scenery is often beautiful.
Springfield is known both as the “Queen City of the Ozarks” and the “Birthplace of Route 66.” Located in south-central Missouri at a strategic crossroads, Springfield was a railroad hub, home to a bloody Civil War battle, and played an important role in the birth of the Mother Road. Route 66 was aligned through the city in 1926, realigned in 1936, and funneled travelers to the many motels and businesses located along the way until I-44 bypassed the city in 1958.
The Kansas section of Route 66 is short but sweet, and manages to pack in several must-see stops in a little under 14 miles (13.2 to be exact). This small stretch passes through three towns—Galena, Riverton, and Baxter Springs—and can be driven in as little as 30 minutes. Kansas is the only state on your journey where the Mother Road isn’t interrupted by the interstate. Don’t miss the only remaining Marsh Arch Rainbow Bridge, several museums, and other small businesses—on Kansas’ stretch of Route 66, you’ll find quality over quantity.
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Galena is one of the most well-preserved towns along Route 66. Home to the Kan-O-Tex gasoline station from Disney’s Cars , the Murals of Galena, and a 1952 Will Rogers Marker, Galena was once a successful mining town. The town was hit hard by the Depression and violent miner strikes. Later, when the town was bypassed by I-44, tourists stopped visiting, the mines closed down, and the population dropped. Today, several historic buildings around town offer a peek into Galena’s rocky past.
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