Once known as the Main Street of America, Route 66 was once the main thoroughfare for travelers and truckers from Chicago to Santa Monica. The road, stretching for 2,448 miles, never failed to satisfy people’s wanderlust with its breathtaking views, roadside diners, neon signs, gas stations, motels, and unique attractions along the way.
With interstate expansion across the U.S., the Route 66 highway was officially decommissioned in 1985. However, traveling historic Route 66 is still possible, and it’s one of the greatest road trips you will experience.
So, hop on board, we’re in for a one-of-a-kind adventure as we cruise in style on an executive coach bus from Santa Monica to Chicago via Old Route 66, hitting every stop along the way.
The Ultimate Route 66 Road Trip from Los Angeles to Chicago
Los Angeles, California: Our journey begins at the Santa Monica Pier, the western end of Route 66. It is home to one of the most famous beaches in the world, as well as the Official Route 66 End of the Trail marker. Visit the famous Ferris Wheel, ride the 1921 Carousel, and admire the view from Pacific Park.
Victorville, California: Our first notable stop is in Victorville, also called “the gateway to the high desert.” This city is also home to the California Route 66 Museum, which displays the history of the highway from its inception to its decommissioning.
Barstow, California: Known as the “Crossroads of Opportunity,” visit the Route 66 Mother Road Museum to learn about the evolution of the road in a small town that has celebrated Route 66 for more than a century. Check out Barstow’s restored Harvey House Railroad Depot.
Needles California: We’re just going to pass through Needles where the famous song “Get Your Kicks on Route 66” was composed.
Amboy, California: Our next stop is the ghost town of Amboy, a former mining and railroad community that gained notoriety for its funky roadside attractions. See Roy’s Motel and Cafe, famous from the movies, and the Amboy Shoe Tree. We’ll stop at the Amboy Crater National Natural Landmark—a 27-square mile lava field in the middle of a dormant cinder cone volcano.
Seligman, Arizona: To soak up some Route 66 nostalgia, we’ll head to Seligman, the town that is rumored to have inspired Radiator Springs in the Pixar movie, Cars. Here, you can visit several retro shops and diners, including the Rusty Bolt, the Snow Cap Drive-In, and the Angel and Vilma Delgadillo’s Route 66 Gift Shop.
Flagstaff, Arizona: Home to the Lowell Observatory, where Pluto was discovered, we’ll stop in historic downtown Flagstaff, filled with quaint cafes, shops, and galleries.
Winslow, Arizona: Picture time! Gather your group to pose with the “Standing on the Corner” statue overlooking the iconic Route 66 mural in downtown Winslow, made famous by the Eagles’ song “Take It Easy.” Across the street is La Posada, a restored 1930s hotel with a museum, gallery, and restaurant. Meteor Crater & Barringer Space Museum is an absolute must-visit.
Holbrook, Arizona: The gateway to the Petrified Forest National Park. Step back in time and explore the prehistoric petrified wood and colorful painted desert. You can see petrified wood, dinosaur fossils, and Route 66 memorabilia at the Rainbow Forest Museum and the Wigwam Motel.
Albuquerque, New Mexico: Home to numerous Route 66 icons such as the El Rey Motor Court, National Museum of Nuclear Science & History, and Old Town Plaza, Albuquerque is known for its hot-air balloon fiesta.
Santa Fe, New Mexico: Our next stop is the capital of New Mexico and a treasure trove of colonial and adobe architecture, Native American art, and scenic landscapes. You can visit the Palace of the Governors, the Cathedral Basilica of St. Francis, and the Georgia O’Keeffe Museum.
Santa Rosa, New Mexico: Time for a pit stop to see the Route 66 Auto Museum and take a dip in the Blue Hole, a natural, deep-water lake that’s popular for scuba diving and swimming.
Tucumcari, New Mexico: Another Route 66 hotspot, Tucumcari brims with vintage neon signs, motels, diners, and murals. You can grab a bite at the Pow Wow Restaurant and Lounge, browse through the Mesaland Community College Dinosaur Museum, or snap photos of the Tee Pee Curio Shop and the Blue Swallow Motel.
Glenrio, Texas: Glenrio straddles the Texas-New Mexico state line and was once a thriving service town for travelers. You can see the iconic First Motel in Texas, the Route 66 Texas-New Mexico Welcome Center, and the remains of the Spencer Theatre.
Amarillo, Texas: In the heart of Texas, Amarillo will amaze you with its funny and quirky culture. You can take a selfie with the giant Cadillac Ranch, visit the American Quarter Horse Hall of Fame, or savor a juicy steak at the Big Texan Steak Ranch.
Shamrock, Texas: We’ll make a brief stop at Shamrock, a town that boasts the Tower Station and U-Drop Inn Cafe, a famous Art Deco building that was featured in Cars.
Oklahoma City, Oklahoma: Our first stop in Oklahoma is home to Bricktown, a bustling entertainment district with a riverwalk, a canal, and a range of restaurants, bars, and boutiques. We’ll check out the Oklahoma Route 66 Museum, the National Cowboy and Western Heritage Museum, and the Myriad Botanical Gardens if time allows.
Tulsa, Oklahoma: Picture time! Gather around the iconic Blue Whale of Catoosa. We’ll check out the Philbrook Museum of Arty, the Woody Guthrie Center, and take a selfie in front of the Golden Driller statue.
Joplin, Missouri: Driving east, we’ll pass through Joplin’s Route 66 Mural Park. Unfortunately, the famed Route 66 Carousel Park—a classic amusement park—closed in 2014.
Springfield, Missouri: The official Birthplace of Route 66, where the road was named by telegram on April 30, 1926. The city celebrates with an annual festival every August and a variety of other attractions, including the Route 66 Roadside Park. You could also visit Fantastic Caverns, a ride-thru cave, or the original (and massive) Bass Pro Shops with Wonders of Wildlife Museum.
St. Louis, Missouri: A city that speaks to the frontier spirit and the American dream, visit the Gateway Arch—the world’s largest arch. Visit the Missouri Botanical Garden, Grant’s Farm, or tour the Anheuser Busch brewery.
Litchfield, Illinois: As we enter the final state of our roadtrip, we visit the Route 66 Welcome Center, and eat at the Ariston Cafe—the longest-running restaurant on Route 66.
Springfield, Illinois: Picture Time! We’ll grab a selfie with the Lauterbach Giant in the home to the Abraham Lincoln Presidential Library and Museum, Old State Capitol, and Cozy Dog Drive-In, we’ll grab a bite at Motorheads Bar Grill & Museum for the custom cars and vintage signs.
Pontiac, Illinois: Discover the Route 66 Association Hall of Fame & Museum or visit the Pontiac-Oakland Automobile Museum—two venues that showcase the beauty and innovation of classic cars.
Chicago, Illinois: From Santa Monica Pier to Navy Pier, our road trip comes to a close in the Windy City where Lake Shore Drive falls into Lake Michigan. We’ll stop by Millenium Park nearby for a selfie with the Cloud Gate sculpture (the giant shiny metal jellybean). Otherwise, we’ll find plenty to do in one of the world’s most famous cities, with stops at the Museum of Science and Industry, and the Art Institute of Chicago. Maybe we’ll catch a ballgame at iconic Wrigley Field before turning back.
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