Have you been dreaming about taking the ultimate American road trip? America’s “Mother Road” awaits you. Described as the “Main Street of America” the 2,448-mile (3,940 km) U.S. Route 66 road trip is more than just an ordinary journey.
It is a symbol of America—of freedom, history, hope, and the American Dream. In this article, you’ll learn everything you need to know to plan the ultimate Route 66 road trip.
Established in 1926, Route 66 is one of American most famous routes for a road trip. It interlinks no less than eight American states and hundreds of cities, small towns, and counties. Connecting Chicago to Los Angeles, it is one of the longest continuous highway stretches in the country.
States covered by U.S. Route 66: Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona, and California.
What makes this road so special? Why does it have a special place in the American heart? A history of hope and the promise of a better life.
During the dark times of the Great Depression, this road provided an opportunity to millions of poverty-stricken Americans fleeing the Dust Bowl to look for a better life in the West. John Steinbeck’s iconic novel “The Grapes of Wrath” —which was based on one such story of migration from Oklahoma to California—popularized the term the Mother Road for Route 66.
Get ready for a journey through the heart of America—from the bustling streets of Chicago to the sunkissed shores of California. Here’s how you plan your U.S. Route 66 road trip.
Note: For more details about how to plan a grand road trip in America, check out our guide “The Great American Road Trip: 7 U.S Routes to Explore Before You Die!”
Windy City Wonders: Big Slices and Big Shoulders in Chicago, Illinois
Your journey begins in the “Windy City” of Illinois, Chicago at 122 South Michigan Avenue.
Note: [You could start the trip the other way round in Los Angeles but most travelers like to begin in Chicago heading westbound—like those who escaped the Dust Bowl in the Midwest].
Before you set out, we recommend that you spend a day exploring the City of Big Shoulders AKA Windy City Chicago. Here’s what you can do.
- Explore the Millenium Park. Known for its free concerts, art installations, and the iconic Cloud Gate sculpture known as “the Bean.”
- Stroll Along the Navy Pier: A popular place for tourists featuring boat tours, a Ferris Wheel, and trendy restaurants.
- Visit the Art Institute of Chicago: Check out the vast American Gothic painting collection.
- Take a Chicago River Cruise or enjoy thrilling views of the city’s skyline on the 103rd floor of the Willis Tower Skydeck.
- Deep Dish Chicago-Style Pizza: Try the quintessential Chicago culinary icon at Lou Malnati’s Pizzeria.
Pit Stop in Pontiac: Museums, Murals, and Mother Road History
After frolicking in Chicago, we arrive after a 100-mile (90 min drive) at our first important Route 66 stopover— the city of Pontiac. A city so steeped in the lore of the Mother Road that it has built a museum to honor it. The Route 66 Hall of Fame Museum features memorabilia commemorating the history of the road.
If you are interested in automobiles and their history, consider visiting the Pontiac Oakland Auto Museum, which showcases the history of the Pontiac car. You can enjoy free trolley rides downtown, grab a quick bite, and see the famous Pontiac city murals before you get back on the road.
Through the Arch of Greatness: “The Show-Me State” Missouri
After a 3-hour (200-mile) drive, we arrive at St. Louis (Missouri) known for the tallest man-made monument in all of America—the Gateway Arch, built to celebrate the westward expansion of the country. You can catch a ride to the top of the Arch to enjoy magnificent views of both sides of the Mississippi River. Other points of interest include the Missouri City Museum which showcases many items that shed light on Route 66 history.
Located southwest of St. Louis is the “City of Murals” Cuba (1 hr 15 min drive/ 80 miles). Pull over to see the stunning murals that depict the region’s history and culture. The town is also home to one of the oldest continuously operating motels on Route 66—the Wagon Wheel Motel.
Mines, Minerals, and Memories: Galena, Kansas
Interestingly for all of the 2,448 miles of Mother Road, only 13.2 miles run through Kansas before entering Oklahoma. The highlight of this leg of the trip is a service station called Cars-on-the-Route featuring vehicles inspired by the movie “Cars.”
To catch a quick feel of Kansas, pull over to the town of Galena which boasts a rich history of mining.
Oklahoma: Cowboys, Tulsa Tango, and ‘Yeehaw’ in OKC
A 100 miles later we arrive at the Oklahoman town of Tulsa, best known for its Art Deco architecture dating back to the 1920s and 1930s. If you care for Art, visit the Philbrook Museum of Art which is housed in a gorgeous Italian Renaissance Villa.
The capital Oklahoma City (OKC—100 miles/90 min drive from Tulsa) is best known for its southern charm, cattle ranches, entertainment districts, theme parks, and classy museums. The first thing you need to do in OKC is explore the Bricktown Entertainment District characterized by its brick-lined streets. We recommend you spend the night here and explore its hip nightlife and fashionable dining. A fun way to explore the city is through a water taxi in the Bricktown Canal. Back in the day, OKC provided a sophisticated and urbane respite to weary travelers of Route 66.
Learn more about the region’s history as a hub of cattle ranching and inspiration for countless Western movies by visiting the National Cowboy & Western Heritage Museum, and the Oklahoma City Museum of Art.
Wild West Adventures in “The Lone Star State” Texas
After a 4-hour (260-mile) drive we arrive in Amarillo, Texas—best known for its 1974 Cadillac Ranch sculpture which consists of 10 Cadillacs buried nose-first in the ground, inclined on the same angle as the Pyramid of Giza. Road trippers on Route 66 stop here for a photo. If you are a fan of Texas-style steaks, try the Big Texas Steak Ranch in town.
The next important spot on the U.S Route 66 Road trip is the town of Adrian which marks the midpoint of Route 66 (50 miles away). Travelers usually pull over at the Midpoint Cafe to mark the milestone and savor its delicious pies. “When you’re here, you’re halfway there” proclaims the slogan of the cafe which opened up in 1928.
Art, Architecture, and Heritage in the “Cultural Heart of the Southwest”: New Mexico
You arrive in chic and elegant Santa Fe known for its thriving art scene and Pueblo architecture (3.5 hr drive/230 miles drive). Built in 1610 AD, the oldest capital city in the U.S. also lays claim to the title of the “Cultural Capital of American Southwest.” The downtown of Santa Fe—a UNESCO World Heritage Site— is filled with many art galleries, studios, and old Basilicas.
Some points of interest include the Santa Fe Plaza (the cultural and historical hub of the city teeming with centuries-old buildings and landmarks), the Cathedral Basilica of St. Francis of Assisi, the Museum of International Folk Art, New Mexico History Museum, and the Palace of Governors (which is as old as the city itself).
The next important city on Route 66 in New Mexico is Albuquerque (60 miles/1 hour drive). The city prides itself on its more than a dozen museums and a downtown that brims with public art featuring sculptures and murals.
Also See: US route 50 in Nevada!
Arizona Awaits: The Grand Canyon, Desert Dreams, and U.S. Route 66 Heritage
For the next 530 miles, your road winds through arid rangeland, old railway towns, and tribal communities of New Mexico. This is a part of America where Indian tribal, American, and Spanish cultures and histories intermingle, making for a rich cultural experience.
Along the way, you will pass towns like Holbrook which is a gateway to the Petrified Forest National Park. This national park is known for its fossilized ancient trees. A part of Route 66 history is the famous Wigwam Motel in Holbrook. You can spend the night in a concrete Indian Teepee.
The town of Flagstaff, Arizona (famous for the Lowell Observatory which discovered Pluto) serves as a base to explore the Grand Canyon. If you are into Astronomy, the best star-gazing in America happens at this observatory.
Surf, Sands, and the Pacific: Signing Off in Style in Golden State, California
Your epic road trip nears its end as you make your way from arid Arizona to sunny coastal California. In California, the highway runs through cities like Pasadena, Los Angeles, and San Bernardino.
Your Route 66 journey ends at Santa Monica Pier where you finally get to see the magnificent Pacific Ocean. There is a sign on the pier that officially marks the end of the route. Be sure to take a photo at the sign as a souvenir.
If you still have more time to explore California, check out our comprehensive Californian Road Trip Guide.
“California Dreamin’: A Road Trip Down the Pacific Coast Highway.”
[Note: Want to plan a grand road trip along the Pacific Coast Highway? Check out our exclusive guide “California Dreamin’: A Road Trip Down the Pacific Coast Highway”
Conclusion
Get ready to leave the familiar behind, and embark on a trip of exciting adventure. Your life will never be the same after an epic adventure on U.S. Route 66 road trip. The memories you make along the way will stay with you forever.
The perfect deep pan pizza in Chicago, the astonishing Gateway Arch of St. Louis, the murals of Cuba, the art-deco wonders of Tulsa, the classy urban chicness of OKC, the ranches and steaks of Texas, the Southwestern heritage of New Mexico, the Grand Canyon adventures of Arizona, and the sunkissed beach delights of Santa Monica….these are memories of a lifetime!
Buckle up, get ready, gather your friends, and loved ones, and embrace the freedom of the open road.
FREQUENTLY ASKED QUESTIONS ABOUT U.S. ROUTE 66 ROAD TRIP
What is the best time to go on a U.S Route 66 Road Trip?
The best time of the year to go on a Route 66 road trip is from May to October—(late spring to early fall). Roads are mostly clear and the weather is mild with very few road hazards.
How many days does a U.S Route 66 road trip take?
That depends on your style of travel, the destinations you want to see, and how many stops you want to make along the way. We recommend a minimum of 2 weeks to enjoy all the great historical sights, monuments, natural wonders, and cultural landmarks. However, if you are in a hurry, you’ll need a minimum of 7-10 days.
What are some of the “Cant-Miss” destinations on a U.S Route 66 road trip?
Here’s a list of some important stopovers on U.S Route 66 road trip.
- Illinois: Chicago (Millennium Park, Navy Pier, Chicago River Cruise). Pontiac (Route 66 Hall of Fame Museum, Pontiac Oakland Auto Museum)
- Missouri: The Gateway Arch, Missouri City Museum, “City of Murals” Cuba
- Oklahoma: Oklahoma City (Bricktown Entertainment District, Bricktown Canal water taxi), Tulsa’ Philbrook Museum of Art.
- Texas: Amarillo (Big Texas Steak Ranch and the Cadillac Ranch).
- New Mexico: Santa Fe (Santa Fe Plaza, Cathedral Basilica of St. Francis of Assisi, Palace of Governors), Albuquerque.
- Arizona: Holbrook, Flagstaff (Lowell Observatory), Grand Canyon (technically not a part of Route 66 but the detour is worth it).
- Santa Monica: The Santa Monica Pier and the “Route 66 End of Trail” sign.
