U.S. Route 66 Road Trip: Ultimate Adventure on America’s | Mother Road

Why Route 66 Still Earns Every Word Written About It

There is a version of Route 66 that exists purely as mythology: the neon signs, the open desert, the diner pie, the freedom of the open road. And then there is the actual drive, which is longer, stranger, more historically dense, and more genuinely moving than the mythology prepares you for. I have done both and they are not the same trip.

Route 66 was established in 1926 as one of the original US Highway System roads, connecting Chicago on Lake Michigan to Santa Monica on the Pacific Coast.

The 2,448-mile route crosses eight states and has been called the Main Street of America because of what it once represented: a through-line connecting the agricultural Midwest to the industrial cities of Illinois and eventually to the promise of California.

During the Great Depression, John Steinbeck named it the Mother Road in The Grapes of Wrath because it was the road that carried hundreds of thousands of Dust Bowl refugees westward toward what they hoped would be a better life.

That history is not abstract. You feel it in the landscape.

Route 66 is the only road in America where the history of the road itself is as interesting as anything alongside it. Every mile carries the weight of the people who drove it before you.

The route was officially decommissioned in 1985 when the interstate highway system made it redundant. What remains is a patchwork of state roads, many of them still driveable, that the National Park Service now manages as the Route 66 Corridor Preservation Program.

Driving the original alignment rather than the interstate requires planning and a tolerance for occasional gravel sections and unmarked junctions.

It is worth both.

States covered by U.S. Route 66: Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona, and California.

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!”

Chicago: Where the Mother Road Begins

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.

The official start of Route 66 is at the intersection of Adams Street and Michigan Avenue in downtown Chicago, marked by a sign that most people photograph from the sidewalk before heading west. Spend a full day in Chicago before you start driving. The city earns the time independently of the road trip and arriving unhurried into the Midwest of Illinois, Missouri, and Kansas with Chicago properly experienced behind you changes the emotional logic of the whole journey.

Millennium Park on Michigan Avenue holds the Cloud Gate sculpture, universally known as the Bean, which reflects the Chicago skyline and anyone standing in front of it in a distorted mirror image that has been photographed approximately a billion times and somehow remains worth photographing again.

The Art Institute of Chicago on the same block is among the five best art museums in the United States with a collection that runs from Georges Seurat to American Gothic.

Navy Pier on the lakefront handles the more tourist-facing version of Chicago with boat tours, a 196-foot Ferris Wheel, and a waterfront walk that is genuinely pleasant regardless of the crowd density.

Lou Malnati’s Pizzeria on North Wells Street in River North is where the deep-dish question gets settled. The Chicago-style deep dish is a specific product that does not translate well to description and must be experienced to be evaluated honestly. Order it with the sausage. Eat it before you leave the city. The memory of it will be useful somewhere in the desert sections of Oklahoma.

STARTING POINT NOTE:

Most Route 66 guides recommend driving west to east, Chicago to Santa Monica, to follow the historical direction of the Dust Bowl migration. This also keeps the setting sun in your windshield through the desert sections of the Southwest, which is the direction that makes the landscape photographs work best in the late afternoon.

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.

Illinois to Missouri: Pontiac, St. Louis and the Gateway Arch

Pontiac, Illinois sits 100 miles southwest of Chicago and functions as the first proper Route 66 stop for people who want to engage with the road’s own history. The Route 66 Hall of Fame and Museum on the main street documents the culture of the road through memorabilia, signage, photographs, and personal effects from the people who drove it, worked it, and lived alongside it during its peak decades.

The Pontiac Oakland Auto Museum next door covers the history of the Pontiac automobile brand in a collection that appeals directly to the section of the Route 66 audience that approaches this trip from the automotive end.

St. Louis, Missouri sits 300 miles further west and announces itself with the Gateway Arch rising 630 feet above the Mississippi River on the downtown waterfront.

The arch was completed in 1965 as a monument to the westward expansion of the United States and it functions exactly as intended: as a physical representation of the idea that the continent opens up on the other side of the river. The tram ride to the top runs through the interior of the arch structure and the observation windows at the summit give views in both directions across the city and the river that justify the experience entirely.

Missouri History Museum in Forest Park covers the Lewis and Clark expedition and the history of the Louisiana Purchase territory in a collection that provides useful context for what the landscape means as you continue west.

The Gateway Arch at sunrise from the Illinois side of the Mississippi is the photograph that sells itself. The actual view from the observation windows at the top is something the photographs do not fully prepare you for.

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.

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: Tulsa Art Deco and Oklahoma City’s Bricktown

Oklahoma occupies a specific place in the Route 66 story because it is the state that the Dust Bowl migrants were leaving. The drought and topsoil erosion of the 1930s devastated the agricultural economy of the Oklahoma panhandle and surrounding region and the families who loaded their belongings onto cars and trucks and drove west on Route 66 were primarily from here.

Driving through Oklahoma in the other direction with that context in mind gives the landscape a different weight.

Tulsa is the first major Oklahoma City on the route and holds an extraordinary concentration of Art Deco architecture from the 1920s and 1930s, built during the oil boom that followed the discovery of petroleum in the region. The Boston Avenue Methodist Church from 1929 and the Philbrook Museum of Art, housed in a 1927 Italian Renaissance villa that oil baron Waite Phillips donated to the city in 1938, are the two buildings that represent Tulsa’s architectural peak most clearly.

The Philbrook collection covers American, Native American, and decorative arts in a setting that makes the experience more like visiting a particularly well-appointed private estate than a conventional museum.

Oklahoma City, 100 miles southwest of Tulsa, runs a different energy from Tulsa’s architectural formality.

The Bricktown Entertainment District in downtown OKC was converted from a 19th-century warehouse district into a restaurant and music venue complex connected by a canal where water taxis run between the main entertainment stops. The National Cowboy and Western Heritage Museum northeast of downtown holds the most comprehensive collection of Western American art and cowboy culture artifacts in the country, covering everything from Frederick Remington bronzes to working saddles.

Texas and New Mexico: Cadillac Ranch to Santa Fe

Wild West Adventures in “The Lone Star State” Texas

Amarillo, Texas is where Route 66 delivers one of its most specific and deliberately absurd landmarks. Cadillac Ranch, located on the west side of town in a field beside I-40, consists of ten Cadillacs buried nose-first in the ground at the same angle as the slope of the Great 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.

The sculptor Chip Lord installed them in 1974 as a commentary on American car culture and consumerism.

You can see the cars now covered in layers of spray paint applied by visitors over five decades. You are welcome to add your own. Bring a can. The Midpoint Cafe in Adrian, 50 miles west of Amarillo, marks the halfway point of the entire 2,448-mile route. The pie is made in-house and the sign outside proclaims: when you are here, you are halfway there.

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.”

Santa Fe, New Mexico is the cultural stop that changes the register of the whole trip. Founded in 1610 as a Spanish colonial capital, it is the oldest state capital in the United States and holds UNESCO World Heritage status for its historic downtown. The Santa Fe Plaza is the geographic and social centre of the old city, surrounded by buildings that have stood since the 17th and 18th centuries.

The Palace of Governors on the north side of the plaza is the oldest continuously occupied government building in the United States, built in 1610.

The Cathedral Basilica of Saint Francis of Assisi two blocks east was commissioned by Archbishop Jean-Baptiste Lamy in 1869 and the Romanesque design sits in deliberate contrast to the adobe architecture surrounding it.

Santa Fe is where Route 66 stops being a drive through American history and starts being a walk through it. The buildings are the history. The streets are the history. The whole place demands you slow down.

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.

Some roads are just roads, but US Route 50 cutting through Nevada is the kind of drive that gets under your skin and stays there. Empty, vast, and quietly unforgettable in a way that busy highways never could be. You should check it out

Arizona: Petrified Forests, Flagstaff and the Grand Canyon Detour

The Arizona section of Route 66 runs through the Colorado Plateau and the quality of the light changes noticeably from New Mexico once you cross the state line. The high desert here sits at 5,000 to 7,000 feet and the air is drier and clearer than the sections behind you.

Holbrook sits at the junction of Route 66 and the entrance road to Petrified Forest National Park, which protects 220 square miles of ancient landscape containing fossilized trees from the Triassic period approximately 225 million years old.

The Painted Desert section of the park runs along the northern edge in bands of red, orange, purple, and white that represent different layers of the geological record exposed by erosion.

Flagstaff is the largest city on the Arizona section of Route 66 and functions as the base for a Grand Canyon excursion that is technically a detour but practically essential. The canyon sits 80 miles north of Flagstaff via Highway 180 and the South Rim is accessible year-round.

Lowell Observatory, where astronomer Clyde Tombaugh discovered Pluto in 1930, sits on Mars Hill above the city and runs public viewing sessions through its historic telescopes on clear evenings.

Flagstaff holds a Dark Sky City designation and the observatory experience is the best urban stargazing available anywhere on the Route 66 corridor.

Final stop on the U.S. Route 66 Road Trip - The Golden State California

California: Santa Monica Pier and the End of the Road

Surf, Sands, and the Pacific: Signing Off in Style in Golden State, California

The final section of Route 66 runs through the Mojave Desert before dropping into the Los Angeles basin through San Bernardino and Pasadena. The quality of the driving changes here because the traffic density increases steadily as you approach the city and the open road feeling of the desert sections gives way to the stop-and-start reality of Southern California highways.

This is appropriate rather than anticlimactic.

The Mother Road ends in a city, which is where the Dust Bowl migrants were headed and where the American Dream the road carried was supposed to be redeemed.

Santa Monica Pier on the Pacific Ocean marks the official end of Route 66. The sign at the pier reads: End of the Trail. Stand in front of it. Take the photograph. Then walk to the end of the pier and look west across the Pacific. The continent is behind you and 2,448 miles of American history, geography, and culture are in the rearview mirror. That is not a small thing to have done.

Have you driven Route 66 or any section of it?

Did you add a layer to the Cadillac Ranch in Amarillo, eat pie at the Midpoint Cafe, or stand at the Santa Monica sign at the end of the trail?

Drop your experience in the comments below.

FAQs and Backlink Resources

How long does a Route 66 road trip take?

A minimum of 2 weeks is recommended to stop meaningfully at the major points along the route. A rushed 7 to 10 day drive is possible but sacrifices most of what makes the trip valuable. Families with children doing worldschooling or homeschooling content along the way should allow 3 to 4 weeks.

Is Route 66 still driveable today?

Yes, approximately 85 percent of the original Route 66 alignment remains driveable. Some sections require leaving the interstate and following state road signs marked with the Route 66 shield. The Historic Route 66 Association maintains updated alignment maps. The National Park Service Route 66 Corridor Preservation Program documents which sections are intact.

What is the best time of year to drive Route 66?

Late spring from May through June and fall from September through October are the best windows. Summer is peak season but the Arizona and New Mexico desert sections reach extreme temperatures in July and August. The shoulder seasons offer mild temperatures across all eight states and fewer crowds at the major stops.

What is the best way to navigate the original alignment?

The National Historic Route 66 Federation website and the EZ66 Guide by Jerry McClanahan are the two most reliable navigation resources for the original alignment. GPS systems default to interstate routing and will not take you along the historic road sections without specific input.