The open road has long symbolized freedom and adventure, and there’s no road that embodies this spirit quite like Route 66. Often called the "Mother Road," Route 66 has a near-mythical presence in American culture. With its neon-lit motels, quirky roadside attractions, and vast, scenic landscapes, it offers travelers a nostalgic trip back to a time when road trips were the ultimate form of adventure.

Spanning eight states and 2,448 miles, Route 66 connects captivating sights, small-town charm, and larger-than-life landmarks. Here, we guide you through must-see stops and explain why this highway remains such an enduring symbol of exploration and Americana.

A Brief History of Route 66

First established in 1926, Route 66 was one of the original highways in the U.S. Highway System. Stretching from Chicago, Illinois, to Santa Monica, California, it quickly became a vital artery for economic growth, connecting rural and urban communities across the heart of the country.

During the Great Depression and the Dust Bowl migration of the 1930s, Route 66 earned its nickname "The Main Street of America." Families seeking a brighter future traveled west along its lanes, transforming the road into a lifeline of hope. By the 1950s, Route 66 was thriving, lined with diners, motels, roadside attractions, and gas stations—all vying for the attention of travelers.

Although the highway was officially decommissioned in 1985 with the introduction of the Interstate Highway System, its cultural and historic significance lives on. Travelers still flock to the route to experience its nostalgic charm, timeless landmarks, and the open-road spirit that defined an era.

Must-See Stops Along Route 66

Every mile of Route 66 has a story to tell. Here are some of its most iconic and scenic stops, explained in vivid detail to help you picture the adventure that awaits.

1. Chicago, Illinois

Start your trip at the eastern terminus in Chicago, where a "Begin Route 66" sign marks the start of your epic road trip. Before hitting the highway, explore the vibrant city. Enjoy deep-dish pizza at a famous eatery like Lou Malnati’s or grab a classic hot dog from Portillo’s. Landmarks like The Bean in Millennium Park or the Willis Tower Skydeck offer unparalleled views of the Chicago skyline. Once you’ve soaked in the energy of this bustling city, it’s time to head west into quieter terrain.

2. Pontiac, Illinois

Route 66 thrives on small-town charm, and Pontiac delivers it in spades. This picturesque town is home to the Route 66 Hall of Fame and Museum, where visitors can trace the highway’s fascinating history. The city streets are also lined with gorgeous murals depicting scenes from Route 66’s storied past. Don’t miss the chance to snap a photo with one of the vintage cars parked throughout the town.

3. St. Louis, Missouri

You can’t travel Route 66 without a stop in St. Louis, home to the iconic Gateway Arch, symbolizing the westward expansion of America. For those who appreciate quirky attractions, a visit to Ted Drewes Frozen Custard is a must—indulge in a "concrete," a thick custard treat that’s a local favorite. To stretch your legs, cross the Chain of Rocks Bridge, a unique, bending bridge that once carried Route 66 traffic across the Mississippi River.

4. Catoosa, Oklahoma: The Blue Whale

The Blue Whale of Catoosa is one of the most memorable and whimsical stops on Route 66. Built as a love letter in the 1970s, this giant smiling whale is perched on a serene pond, offering visitors both a delightful roadside attraction and a peaceful picnic spot. It's a destination that embodies the playful, quirky charm of Route 66.

5. Oklahoma City, Oklahoma

As you roll into Oklahoma City, you’ll find a rich blend of cowboy heritage and urban sophistication. Explore the National Cowboy & Western Heritage Museum to immerse yourself in the history of the American West. For Route 66 history, head to the Milk Bottle Grocery, a tiny building topped with—you guessed it—a giant metal milk bottle. It’s a nostalgic photo opportunity worth stopping for.

6. Amarillo, Texas: Cadillac Ranch

One of Route 66’s most iconic and surreal landmarks, Cadillac Ranch is an open-air art installation featuring ten Cadillacs buried nose-first in the Texas desert. Visitors are encouraged to bring spray paint and leave their mark on this vibrant, interactive monument. It's a must-see, combining modern art with the rebellious, creative spirit of the Mother Road.

7. Tucumcari, New Mexico

Tucumcari is perhaps the quintessential Route 66 town. Its streets are adorned with retro neon signs, vintage motels, and murals celebrating the area’s history and culture. The Blue Swallow Motel, a historic gem, exudes old-school charm. Staying here feels like stepping back into the 1950s, complete with shining classic cars parked by its brightly lit rooms.

8. Santa Fe, New Mexico

A slight detour will take you to Santa Fe, an artsy town with a unique blend of Pueblo and Spanish colonial architecture. Its historic plaza, filled with galleries, museums, and street vendors, captures the essence of the Southwest. Whether you’re browsing handmade turquoise jewelry or savoring authentic Southwestern cuisine, Santa Fe is a cultural treasure worth exploring.

9. Holbrook, Arizona: Wigwam Motel

Holbrook offers a stop that’s both historic and whimsical—the Wigwam Motel. Guests can stay in lodging shaped like teepees, a classic Route 66 experience. These cozy units are surrounded by vintage cars, adding to the nostalgic charm. It's an unforgettable way to spend a night on your road trip.

10. The Grand Canyon, Arizona

Although not directly on Route 66, a short detour to the Grand Canyon is an essential addition to your itinerary. Standing at the rim of this natural marvel is a humbling experience, with panoramic views that are sure to leave you breathless. Whether you hike the trails or simply take in the vistas, the Grand Canyon is a true world wonder.

11. Oatman, Arizona

Step back in time with a stop in Oatman, a quirky mining town tucked into Arizona’s rugged mountains. Wild burros roam the streets, descendants of the pack animals once used by miners. The Old West ambiance of Oatman, complete with staged gunfights, will transport you to another era.

12. Santa Monica, California

Finally, your Route 66 adventure culminates at the Santa Monica Pier. The "End of the Trail" sign marks the conclusion of your epic road trip. Celebrate with a walk along this historic pier, enjoy a ride on the Ferris wheel, or dip your toes into the Pacific Ocean as you reflect on the miles traveled and memories made.

Few roads can lay claim to the cultural significance and spirit of adventure that Route 66 represents. It’s more than a route—it’s a symbol of freedom, exploration, and the thrill of the open road. From bustling cities to sleepy towns, towering natural wonders to delightfully quirky attractions, Route 66 captures all that makes America worth exploring. Traveling this road isn’t just about the destination; it’s about savoring every mile along the way.