A Route 66 road trip is a unique adventure where each turn reveals a new chapter in the tale of the Mother Road. When you travel this ribbon of asphalt that connects Chicago to Santa Monica, your journey through the heart of America is also a trip through American history.
Embarking on a Route 66 road trip is like flipping through the pages of an American storybook, where each mile marker is a sentence and every town a chapter of history and culture. This journey begins in the bustling streets of Chicago, where the towering skyscrapers and pulsating energy of the Windy City set the stage for an adventure across the heart of America. As you venture along the Mother Road, you’ll see golden plains, snow-capped mountains and barren deserts. And you’ll see a combination of historical gems, quirky roadside attractions and dilapidated icons.
Starting point: Chicago
The Windy City is where the legendary Route 66 begins. As a beacon of commerce and industry in the early 20th century, Chicago mirrors the spirit of Route 66. Its towering skyscrapers, like the Willis Tower, are architectural marvels that symbolize the American dream.
Start your Route 66 road trip with a selfie at the Begin sign outside the Art Institute of Chicago. At this historic spot, you’re not just starting an epic road trip — you’re standing at the threshold of an important piece of American history.
Route 66 in Illinois
As the Chicago skyline fades in your rearview mirror, the historic route will take you southwest from Chicago to St. Louis, winding historical sites and quirky roadside attractions. Be sure to stop at the Route 66 Hall of Fame in Pontiac, where you can explore exhibits and artifacts that celebrate the history of the highway. In Collinsville, you’ll find the world’s largest catsup bottle that doubles as a water tower. And watch for the Muffler Men, larger-than-life fiberglass statues, as you travel throughout the state.
“When you’re passing through Springfield, the Old State Capitol, Lincoln’s Grave and Lincoln’s Home are obligatory stops for history buffs. The Capitol and Home offer tours, while the monument is something you can easily explore on your own.”
— Michelle Price, Honest and Truly
When motoring through the Land of Lincoln on Route 66, take some time to explore the capital city of Springfield, where history intertwines with the road trip culture of the famed highway. Be sure to visit Lincoln’s home and final resting place at the Oak Ridge Cemetery.
Route 66 in Missouri
In the Show Me State, your Route 66 road trip will begin in St. Louis and end in Joplin. Stop at the Chain of Rocks Bridge as you start this portion of your journey. Now a pedestrian bridge, it offers fantastic views and a sense of the original Route 66 spirit.
In Stanton, the Meramec Caverns are famed as a hideout for Jesse James. The Route 66 Car Museum in Springfield showcases over 100 vintage cars, and you can admire a delightful recreation of a 1930s Sinclair gas station in Ash Grove.
For a unique cinematic experience, the Route 66 Drive-In Theatre in Carthage is a throwback to simpler times. Enjoy a movie under the stars in this nostalgic setting. And, as you approach Joplin, the Route 66 Mural Park offers a perfect backdrop for a memorable photo, capturing the spirit of your Missouri Route 66 adventure.
Route 66 in Kansas
Route 66 barely nicks Kansas’s southeastern corner, running just under 13 miles through the Sunflower State. But in that distance, it runs through three towns rich with cattle, mining and Route 66 history. Stop at the Brush Creek Bridge just north of Baxter Springs. It’s the last remaining fixed marsh rainbow arch bridge left on Kansas Route 66.
Route 66 in Oklahoma
Beginning in Miami and ending just west of Sayre, the Sooner State is home to the longest driveable stretch of Route 66. As your Route 66 road trip continues through Oklahoma, notable stops include the Coleman Theatre, a beautifully restored vaudeville and movie palace, and the Route 66 Vintage Iron Motorcycle Museum, filled with classic bikes and memorabilia.
“Whether you’re traveling the Mother Road or just exploring the city, Tulsa has a number of Route 66 gems you won’t want to miss. A stop at Buck Atoms Cosmic Curios is a must when shopping for souvenirs, and the Route 66 Historical Village offers a way to learn about this piece of local history in an open-air museum setting.”
— Megan Bannister, Olio in Iowa
In Catoosa, you’ll see a blue whale that begs you to stop for a photo you can share with a clever Route 66 caption. Just a few miles later, Tulsa is packed with can’t miss sights along Route 66, including murals, statues, museums and other experiences that capture the spirit of the Mother Road.
Route 66 in Texas
As Route 66 carves its way through the Texas Panhandle, it blends iconic landmarks and unique Texan charm. One of the most famous sights is Cadillac Ranch. Near Amarillo, you’ll find this quirky art installation. It invites visitors to leave their mark on ten Cadillacs buried nose-first in the ground and add to its colorful history. Then head to The Big Texan Steak Ranch in Amarillo, famous for its 72-ounce steak challenge. Not only is Amarillo the largest city on the stretch of Route 66 that runs through Texas, but the size of its steaks helps prove that everything is bigger in Texas.
As you motor through Adrian, don’t miss the Route 66 Midpoint sign directly opposite the Midpoint Cafe. This fantastic photo op indicates that you are halfway between Chicago and Los Angeles on your Route 66 road trip.
Route 66 in New Mexico
Route 66 enters New Mexico just east of San Jon and exits just west of Gallup. One of the most notable stops in the Land of Enchantment is the town of Tucumcari. It’s known for its iconic Route 66 murals and neon signs, the Blue Swallow Motel and decaying landmarks from long ago.
Further along, in Santa Rosa, the Route 66 Auto Museum is a paradise for car enthusiasts, showcasing a collection of classic and vintage cars in pristine condition. The town’s Blue Hole, a stunning natural artesian spring, offers a refreshing break from the road.
Route 66 in Arizona
Arizona’s stretch of Route 66 is a mesmerizing journey through landscapes that blend natural wonders with historic charm. The Petrified Forest National Park and Painted Desert present a stunning panorama of colors and geological marvels, showcasing one of the most scenic stretches of a Route 66 road trip. These ancient landscapes, where petrified wood and unique rock formations tell a story millions of years old, are a testament to nature’s artistry.
In Winslow, the famous corner immortalized in the Eagles’ song “Take It Easy” is a must-visit, along with the beautifully restored La Posada Hotel, offering a glimpse into the luxurious past of rail travel. You’ll also travel through the historic towns of Oatman and Seligman, where the spirit of the Old West and the Mother Road’s golden age are still alive.
Route 66 in California
The roughly 300 miles of Route 66 meandering through California may be the most diverse as it begins in the Mojave Desert and weaves through the bustling streets of Los Angeles. On the state’s eastern side, the Amboy Crater and the quirky Bottle Tree Ranch in Helendale provide unique photo opportunities amidst stark landscapes. The ghost town of Calico, once a thriving mining town, now stands as a fascinating historical site.
As you approach Los Angeles and make your way to the Santa Monica Pier, take the chance to visit the Wigwam Motel in San Bernardino, a classic example of Route 66 kitsch. Hollywood and its famous landmarks await in the heart of LA, offering a stark contrast to the quiet desert towns. California’s Route 66 is a journey through contrasting worlds, from desolate beauty to urban glamour, encapsulating the diverse spirit of the Golden State.
End point: Santa Monica
America’s Main Street ends in Santa Monica, where the legendary road meets the Pacific Ocean. When you stand at the End of the Trail sign on the Santa Monica Pier, take a moment to reflect on the rich history of Route 66, from its Dust Bowl-era beginnings to its role in American pop culture. On this spot, your great American road trip meets the ocean’s expanse, providing a perfect photo opportunity to commemorate the completion of an epic road trip.
Sage Scott was bitten by the travel bug as a preschooler when her family moved abroad for the first time. Now settled in America’s Heartland, Sage is a travel writer, world wanderer and photographer whose favorite color is golden hour.