, Route 66 might be right up your alley. This legendary diagonal drive between Santa Monica, California, and Chicago, Illinois, takes in some of the country’s most cliché roadside scenes. From neon signs to middle-of-nowhere truck […] "'Pin It")
Best Road Trip Drives: Route 66
Photo: Andreas H.
If you’re looking for a captivating drive through the heart of America (and to get some kicks while doing it), Route 66 might be right up your alley. This legendary diagonal drive between Santa Monica, California, and Chicago, Illinois, takes in some of the country’s most cliché roadside scenes. From neon signs to middle-of-nowhere truck stops, this is truly one of America’s best road trips.
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History
Long before Route 66 was paved in 1926, the road was traversed by the National Old Trails Highway. For three decades before and after WWII, Route 66 earned the name “Main Street of America” because it travelled through small towns, lined by gas stations, restaurants, shops, and tourist attractions. During the time of the Great Depression, hundreds of thousands of families moved west to California along this route.
Beginning in the late 1950s, the interstate highway system was constructed, and piece by piece, Route 66 became less vital to get from point A to point B. Finally, in 1984, Route 66 was decommissioned, and is now designated Historic Route 66.
What you’ll see
Route 66 is 2,448 miles in its entirety — so be prepared to spend some serious time driving. Many people plan 3 or 4 weeks in order to see many of the sights and not feel rushed along the way.
As the road meanders through the country, you’ll see lots of variation in landscape. The route begins in Chicago, where you can see Lake Michigan, Navy Pier, Wrigley Field, and Lincoln Park, as well as your typical big-city skyline. As you travel through the states of Illinois, Missouri, Kansas, and Oklahoma, you’ll pass through small Midwestern towns and larger cities, and see plenty of rural farmland scenery. Passing into the Texas panhandle, the scenery becomes more desert-like, and once you pass over into New Mexico the terrain becomes rockier and more mountainous. Finally, you’ll experience the arid landscape of the California high desert, and end with breathtaking views of the Pacific Ocean in Santa
Where to stop
There are so many potential places to stop along Route 66 that you could easily spend months traversing the historic road. Here are a few interesting places to stop along the way, though there are literally thousands of stops you could make part of your road trip.
Illinois
Photo: Chad Horwedel via CC
While driving through Illinois, you’ll see the Gemini Giant in Wilmington — a large sculpture of an astronaut holding a rocket ship. This is one of several “Muffler Men” that stands alongside Route 66.
When you’re passing through Springfield, take some time to explore the Route History shop and museum to understand more about how Black travelers and residents experienced Route 66 in its heyday.
Missouri
Photo: Daniel Schwen via CC
In Missouri, Route 66 passes through St. Louis. While in town, make sure you check out the 630-foot Gateway Arch, which is the largest of its kind in the world. Take a tram ride to the top of the arch, and you’ll find breathtaking views of the city and surrounding area.
In Sullivan, make a stop at Meramec Caverns (AKA “America’s Cave”) — a 4.6-mile-long cave system that used to be a shelter for Native Americans.
Kansas
Route 66 is only in Kansas for about 13 miles, so there aren’t many notable places to stop. The small town of Galena is the oldest mining town in the state and is home to several museums depicting its prosperous past.
Oklahoma
Stop in Catoosa, Oklahoma, to see the humungous Blue Whale (which is exactly what it sounds like). It was originally built in the 1970s as an anniversary gift from local resident Hugh Davis to his wife Zelta. It’s the perfect place for an Instagram-worthy selfie.
Texas
Photo: Drriss & Marrionn via CC
As the route makes its way through the Texas panhandle, you’ll see what’s known as the Leaning Tower of Texas — a water cooler that was placed intentionally crooked as an ad for a local truck stop.
You can’t leave Texas without a stop at Cadillac Ranch in Amarillo. This 70s art installation features 10 Cadillac models, painted in graffiti and buried nose-first in the sand.
New Mexico
New Mexico offers the perfect place to take a break from your road trip and relax: the Blue Hole in Santa Rosa. This swimming hole sits right off Route 66 and is popular with scuba divers who want to explore the clear depths of the water.
Arizona
Photo: Jerry and Pat Donaho via CC
Fifty thousand years ago, a meteor hit a spot in Arizona that today is called Meteor Crater. This national natural landmark is a must-see if you’re passing through on Route 66.
Also in Arizona, you’ll pass through Petrified Forest National Park and the Painted Desert, both of which offer breathtaking scenery that appears out of this world.
California
In California, make time to stop at Elmer’s Bottle Tree Ranch in Oro Grande. It’s exactly like it sounds: a forest of tree sculptures made from thousands of glass bottles. It’s certainly not something you’ll see every day.
As your journey reaches its conclusion, spend some time at the iconic Santa Monica Pier. The pier is home to Pacific Park, an amusement park with a solar-powered Ferris wheel, a steel roller coaster, and many other rides for visitors of all ages. You can also pose for a picture next to the historic marker that symbolizes the end of Rout 66.
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Whether you are motivated by an interest in history, a passion for the good ‘ol days, or to experience the incredible diversity of people and landscapes along the way, Route 66 offers an unforgettable journey and one of the best road trip experiences the U.S. has to offer.
Catherine Hiles (she/her) is a native Brit living and working in Dayton, Ohio. Cat has written about a variety of subjects, including finance, cars, and parenting. She is a frequent contributor to Dayton Mom Collective, The Penny Hoarder, and WDW Magazine.
Cat lives with her husband, their two kids, and their energetic pitbull mix. She counts running, lifting weights, walking, and reading among her hobbies. See more articles by Cat.