Every good road trip needs a playlist, and a solid music selection is essential on Route 66. For nearly all of its century-long existence, “the Mother Road” and various stops along it have been an inspiration for recording artists—perhaps none more than Woody Guthrie. The Oklahoma native, one of America’s greatest and most foundational songwriters, is best known (aside from “This Land Is Your Land”) for his “Dust Bowl Ballads,” candid portrayals of Great Depression migrants from Oklahoma to California; many of them drove Route 66.
“Route 66 is so iconic, and not just Woody, but other musicians have traveled it going out to California to seek the American dream, essentially,” says Cady Shaw, the director of the Woody Guthrie Center in Tulsa, Oklahoma, a city known as the Capital of Route 66.
From the blues clubs of Chicago to Guthrie’s Oklahoma, all the way to spots in Arizona and California frequented by the Eagles, these are the music-themed attractions to visit along the route—plus a proper playlist to accompany your drive.
The Art Institute of Chicago is the very start of Route 66.
Photo by Page Light Studios/Shutterstock
1. Beginning of Route 66, Chicago
The official start of Route 66 is in downtown Chicago, at the corner of East Adams Street and South Michigan Avenue, right in front of the Art Institute of Chicago. There’s only one song to start your drive with: “(Get Your Kicks on) Route 66.” Enough artists—Bing Crosby, Chuck Berry, the Rolling Stones, John Mayer—have recorded this classic Bobby Troup–written tune that you could practically listen to it all the way to California. But the version to start with is the 1946 rendition from the Nat King Cole Trio. After all, Cole went to high school in Chicago and cut his teeth in the Windy City’s blues clubs before becoming one of America’s greatest recording artists.
While you’re in town, get steeped in Chi-town’s musical legacy by visiting one of its historic clubs, such as Kingston Mines, and take a tour of the legendary Chess Records office, now home to Willie Dixon’s Blues Heaven Foundation.
Where to stay: Chicago Athletic Association
The Chicago Athletic Association, part of Hyatt’s Unbound Collection, is a block up from the start of Route 66, and it’s across the street from Millennium Park, which hosts the Chicago Blues Festival every June.
2. National Museum of Transportation, St. Louis
- Listen to: “Way Down Watson,” by Son Volt
St. Louis is another city with a cherished blues tradition, first made famous by W.C. Handy’s groundbreaking 1914 composition “St. Louis Blues.” (Bessie Smith recorded the definitive version, with Louis Armstrong on cornet, in 1925.)
You can learn more about the Gateway City’s place in music history at the National Blues Museum, but for a more Route 66–specific flavor, head 20 miles west of downtown to the National Museum of Transportation. In the gallery, amid a variety of planes, trains, and automobiles, you’ll find a section of the facade of the Coral Court Motel, a World War II–era Route 66 lodging that earned a spot on the National Register of Historic Places but was torn down anyway in 1993. On your way, cue up “Way Down Watson,” Son Volt founder Jay Farrar’s rumination on the motel’s demolition.
Where to stay: 21c Museum Hotel St. Louis
The Coral Court may be gone, but you can get plenty of culture at the 21c Museum Hotel St. Louis, which has 173 rooms and a striking contemporary art museum.
3. Woody Guthrie Center, Tulsa, Oklahoma
- Listen to: “Tom Joad,” by Woody Guthrie
The Woody Guthrie Center, opened in 2013 in downtown Tulsa lives deep into the life of its namesake troubadour, looking at his songs, his political and social impact, and his enduring influence on American music and culture. “One thing I think is really cool is that things that Woody was talking about in the ’30s, ’40s, ’50s, are still relevant today,” says Center director Shaw. “We’re still talking about social justice, we’re still talking about equality and voters’ rights. So I think people come in, and they realize how relevant Woody still is.”
Given that Guthrie’s music and social activism were so heavily influenced by his experience of living through the Dust Bowl, there are any number of songs that resonate with a Route 66 drive. One of the most enduring is “Tom Joad,” a ballad inspired by the protagonist of the novel The Grapes of Wrath, which John Steinbeck wrote based on his own experiences of reporting on the exodus from the plains. (Steinbeck and Guthrie were mutual admirers.)
Still feeling folky after leaving the Guthrie Center? You can learn about Woody’s most famous protégé next door at the Bob Dylan Center. While Dylan is more often associated with Highway 61, he has also painted scenes from Route 66.
Where to stay: The Mayo Hotel
To really get into the centennial spirit, check into the Mayo Hotel, a downtown Tulsa landmark that opened in 1925, a year before Route 66.
Cadillac Ranch inspired the Boss to write a song by the same name.
Photo by YuniqueB/Shutterstock
4. Cadillac Ranch, Amarillo, Texas
- Listen to: “Cadillac Ranch,” by Bruce Springsteen
One of the most notable of the many quirky public art pieces that appear along Route 66 is Cadillac Ranch, 10 cars covered in graffiti and buried nose-first in the sand outside Amarillo, Texas. The landmark, created by artists Chip Lord, Hudson Marquez, and Doug Michels in 1974, inspired the song of the same title on Springsteen’s 1980 album The River. The tune is a piece of upbeat Americana with undertones of decay—in classic fashion for both the Boss and the Mother Road.
While you’re in town, cue up George Strait’s “Amarillo Morning” or Robert Earl Keen’s version of “Amarillo Highway” as you head over to the GoldenLight Café & Cantina, a roadhouse right on downtown Amarillo’s stretch of Route 66. The venue, which opened in 1946, has hosted artists including Joe Ely and Todd Snider.
Where to stay: The Barfield
The Barfield, an Autograph Collection property, is in a historic downtown tower built by local businesswoman Melissa Dora Oliver-Eakle in 1927.
The Blue Swallow Hotel is a colorful icon of this part of New Mexico.
Photo by Sandra Foyt/Shutterstock
5. The Blue Swallow Motel and Tucumcari Murals, Tucumcari, New Mexico
- Listen to: “Willin’,” by Little Feat
Unless you happen to be from northern New Mexico, odds are you probably only know Tucumcari (population 5,058) from the refrain of Little Feat’s 1971 anthem “Willin’,” in which frontman Lowell George describes a drug-addled trucker’s travels “from Tucson to Tucumcari, Tehachapi to Tonopah.” There’s no monument to George—or Arizona native Linda Ronstadt—in Tucumcari, but you can get a bit of color at the landmark Blue Swallow Motel, which was the subject of one of Dylan’s aforementioned Route 66 paintings. Or you can do a self-guided tour of the dozens of murals around town (keep an eye open for Elvis on the side of the Motel Safari).
Where to stay: The Motel Safari
Aside from that painting of the King, the Motel Safari also has a Rockabilly Suite dedicated to Wanda Jackson, the “Queen of Rockabilly,” who once stayed in that very room.
6. The Musical Highway, Tijeras, New Mexico
- Listen to: The road, man
In an inspired bit of patriotism, back in 2014 National Geographic and the Department of Transportation partnered to install rumble strips on New Mexico State Road 333 (originally part of Route 66) that, when driven over at 45 miles per hour, make car tires vibrate to the tune of “America the Beautiful.” Charming, right? Now for the bad news: The DOT has removed the signage and hasn’t maintained the strips, so drivers can no longer hear the whole song. But make sure you’re doing the right speed, on the eastbound side of the stretch of road east of Exit 170 (between mile markers 4 and 5), and you’ll still hear some of the melody.
Once you’ve heard the rumbling rendition, put a recorded version on your stereo (may we suggest Ray Charles’s take?), turn around and head west into Albuquerque, where you can catch a band at the historic El Rey Theater or the Launchpad.
Where to stay: Hotel El Rancho
John Wayne, Rita Hayworth, and Kirk Douglas are among the movie stars who bunked down at Albuquerque’s Hotel El Rancho, which opened on Route 66 in 1937.
Winslow, Arizona, is well-known for its homage to the debut single by the Eagles.
Photo by Mark Skalny/Shutterstock (L); photo by David Buzzard/Shutterstock (R)
7. Standin’ on the Corner Park, Winslow, Arizona
- Listen to: “Take It Easy,” Eagles
It’s all there in the name of this public park, which celebrates the site-specific lines written by Glenn Frey and Jackson Browne for the debut single by the Eagles, 1972’s “Take It Easy”: “I’m a-standin’ on a corner in Winslow, Arizona/Such a fine sight to see/It’s a girl, my Lord, in a flatbed Ford/Slowin’ down to take a look at me.”
Standin’ on the Corner Park includes a two-story mural, a parked pickup truck, and a statue by artist Ron Adamson that resembles Browne, whose car once broke down in Winslow, inspiring that iconic verse. Time your visit for the end of September, and you can see a couple of days of live music at the long-running Standin’ on the Corner Festival.
Where to stay: La Posada Hotel
Among the many Fred Harvey Company railway hotels architect Mary E.J. Colter designed is Winslow’s beautiful 1930 La Posada Hotel.
Route 66 ends on the West Coast, in Santa Monica, California.
Photo by Karolis Kavolelis/Shutterstock
8. The End of the Trail, Santa Monica, California
- Listen to: “Will Rogers Highway,” Woody Guthrie
The original end of Route 66 was in downtown Los Angeles, but in 1935 it was extended to Santa Monica, and as of 2009 there’s an official “End of the Trail” sign at the entrance to the Santa Monica Pier. Among the Mother Road’s many nicknames is the Will Rogers Highway, after the 1920s and ’30s Hollywood star; a monument to the actor and the road stands in the clifftop park above Santa Monica Beach, a few blocks up Ocean Avenue from the pier.
We’d recommend listening to Guthrie’s “Will Rogers Highway” as you reach the end of what the songwriter called “My Sixty-Six highway, this Will Rogers road.” But you could just as easily put on “Hotel California”—former Eagles guitarist Don Felder has said Route 66 inspired the song’s opening lyrics—or any number of songs, really. Once you hit the end of the road, though, we recommend channeling Guthrie’s troubadour spirit and looking for busking musicians on the pier or the Third Street Promenade. Want to try playing some music yourself? Drop by McCabe’s Guitar Shop to pick up a new (or old) ax; the store also holds concerts, featuring artists such as Alejandro Escovedo, Rufus Wainwright, and Aoife O’Donovan.
Where to stay: The Georgian Hotel
Keep the historic vibe going and check into the Georgian Hotel, an art deco landmark that debuted on Ocean Avenue in 1933 and received a spare-no-expenses update in 2023.
