Take a nostalgic Route 66 journey through America’s epic highway! Our guide covers must-see stops, landmarks, and classic roadside experiences along this legendary route.
Few roads in the world are as iconic as Route 66. Known as “America’s Main Street” or “The Mother Road,” stretches from Chicago, Illinois, to Santa Monica, California, covering nearly 2,500 miles of history, culture, and adventure. Once the lifeblood of American travel before the rise of the interstate highway system, this legendary road still draws thousands of travelers eager to relive a piece of American history. From its heyday in the 1930s to its modern-day status as a bucket-list road trip, it offers an unforgettable journey through the heart of the United States.
For American travelers, the allure of Route 66 isn’t just about getting from point A to point B—it’s about the journey itself. This guide will take you through some of the most iconic landmarks and must-see stops along , ensuring your journey is filled with adventure and discovery.
The Story of Route 66
Established in 1926, this route became one of the first highways in the United States highway system, linking the Midwest with the West Coast. During the Dust Bowl migration of the 1930s, the highway became a vital route for families seeking new opportunities in California. Over the years freedom, exploration, and the American road trip experience.
By the 1950s, with the rise of new highways and faster routes, it began to decline. In 1985, it was officially decommissioned, but its legacy lived on. Today, portions of the highway have been preserved as historic routes, attracting travelers eager to explore its vintage charm and discover the remnants of a bygone era.
The Beginning of Route 66
Chicago, Illinois
Every great Route 66 adventure begins in Chicago, Illinois. The starting point of the road is marked by a sign at the corner of East Adams Street and Michigan Avenue, close to Lake Michigan. Before hitting the road, take some time to explore the Windy City, known for its impressive architecture, deep-dish pizza, and vibrant arts scene. Whether you visit the Willis Tower (formerly Sears Tower) or stroll along Navy Pier, Chicago is a bustling city full of energy and excitement.
Joliet, Illinois: The First Stop
Leaving Chicago, your first official stop along Route 66 is Joliet, Illinois. Known for its historic landmarks and retro roadside attractions, Joliet offers a glimpse into classic Americana. The Route 66 Welcome Center in Joliet is a must-visit, offering travelers maps, guides, and memorabilia to start their journey right. While in town, don’t miss the opportunity to snap a picture in front of the Joliet sign or visit the Rialto Square Theatre, a beautiful piece of architectural history.
Pontiac, Illinois: A Route 66 Time Capsule
Further down the road, Pontiac, Illinois, is a treasure trove of Route 66 history. The town is home to the Illinois Hall of Fame and Museum, where travelers can learn more about the history of the highway and its importance to American travel. Pontiac is also famous for its colorful murals, which depict scenes from the heyday of Route 66. These murals serve as great photo opportunities, offering a charming backdrop to your road trip memories.
St. Louis, Missouri: Gateway to the West
As you continue your journey, you’ll arrive in St. Louis, Missouri, where the Gateway Arch marks the symbolic starting point of the American West. Standing 630 feet tall, the arch is the tallest man-made monument in the U.S., and you can even take a tram ride to the top for panoramic views of the city. St. Louis is also known for its blues music and barbecue, so make sure to explore its vibrant culture before heading back on the road.
Cuba, Missouri: A Roadside Art Gallery
Dubbed “Mural City,” Cuba, Missouri is a small town that packs a big punch when it comes to artistic flair. The town’s streets are lined with large murals depicting historical scenes and famous figures, offering travelers a unique visual experience along Route 66. Cuba is also home to several vintage motels and diners, allowing you to step back in time and experience what life was like for travelers in the 1950s.
Oklahoma City, Oklahoma: Historic Heartland
One of the larger cities on the journey, Oklahoma City offers a blend of history, culture, and modern attractions. The Oklahoma Route 66 Museum in Clinton, just outside the city, is a great stop for those wanting to dive deeper into the history of the highway. Oklahoma City is also known for its Western heritage, and visiting the National Cowboy & Western Heritage Museum will give you a taste of cowboy culture that’s central to the state’s identity.
Amarillo, Texas: Cadillac Ranch
Texas offers some of the quirkiest attractions and Cadillac Ranch near Amarillo is one of the most famous. This roadside art installation features ten vintage Cadillacs buried nose-first into the ground, and visitors are encouraged to leave their mark by spray-painting the cars. Amarillo is also home to the Big Texan Steak Ranch, a must-stop for those looking for a true Texas-sized meal. If you’re feeling brave, you can attempt their legendary 72-ounce steak challenge.
Santa Fe, New Mexico: A Detour Worth Taking
Although this Route was rerouted in the 1930s to bypass Santa Fe, taking the scenic detour through this historic city is well worth it. As the oldest capital city in the United States, Santa Fe is known for its adobe architecture, vibrant art scene, and rich cultural heritage. Take some time to explore the Santa Fe Plaza and the Georgia O’Keeffe Museum, both of which offer a deeper understanding of the region’s artistic and cultural significance.
Flagstaff, Arizona: Gateway to the Grand Canyon
Continuing west, Flagstaff, Arizona offers a refreshing change in scenery with its mountain vistas and cooler climate. Known as the “gateway to the Grand Canyon,” Flagstaff is a perfect stop for those looking to explore one of the Seven Natural Wonders of the World. But even if you’re not venturing to the Grand Canyon, Flagstaff is full of attractions, including the Lowell Observatory, where Pluto was discovered, and the charming downtown area with its local shops and cafes.
Santa Monica, California
After traveling through deserts, mountains, and plains, your journey on this highway ends at the Pacific Ocean in Santa Monica, California. The iconic way sign at the Santa Monica Pier marks the end of the line, and it’s the perfect place to reflect on your cross-country adventure. The pier itself offers plenty of attractions, from its amusement park to seafood restaurants, where you can enjoy a meal with an ocean view. The nearby beach is a great spot to relax after your epic road trip across America.
https://www.nps.gov/articles/route-66-overview.htm
Traveling along this epic highway is more than just a road trip—it’s a journey through American history and culture. From the bustling streets of Chicago to the sun-drenched shores of California, every mile of the Mother Road offers a glimpse into the past and a chance to experience the diverse landscapes and communities that make up the United States. Whether you’re traveling for nostalgia, adventure, or discovery.
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