The Ultimate Route 66 Playlist

A Route 66 Playlist. Songs from the mother highway. America’s main street. Will Rogers Highway. Fodder of legends and romanticizations since the dawn of the road trip.

Because who hasn’t fantasized about the great American road trip? I sure have. And yet, despite dreaming about such a trek, when I first set out on my own Route 66 road trip, I found that I was terribly under-informed as to what exactly this route historically meant, and what it is now today.

When it was established on November 11, 1926, the highway ran from Chicago, Illinois, through Missouri, Kansas, Oklahoma, Texas, New Mexico, and Arizona before ending in Santa Monica, California; a total of 2 228 miles (3 940 km). In the 1930s, the road served as a major dustbowl route for people heading west in search of better prospects. Because of this, the route experienced a boom and was a major hotspot for roadside businesses.

However, due to the Interstate Highway System, Route 66 began to be lost to time, with large sections of it either being replaced or bypassed entirely.

Today, hints of this once-well-trodden route remain. In the southern states, you’ll find roadside shacks brimming with Route 66 memorabilia, signs in towns such as Santa Monica and Williams, AZ alike. If you look for Route 66, you’ll find a whole kitschy culture just waiting to be explored. And what’s a road trip without some tunes?

So whether it is a song directly about Route 66, by a musician from a Route 66 state, or simply influenced by America’s main street…

The Ultimate Route 66 Playlist

*(Scroll to the bottom to find the playlist in Spotify form!)*

The Rolling Stones – (Get Your Kicks On) Route 66

Written in 1946 by American songwriter Bobby Troup, “(Get Your Kicks On) Route 66” was initially recorded and became a hit by Nat King Cole the same year. The song lyrics follow the path of Route 66 from Chicago to Los Angeles.

Eagles – Take It Easy

If you listen to the Eagles incarnation of this Jackson Browne classic, you’ll get an earful about a little town on Route 66 named Winslow, Arizona; a reference that apparently draws more visitors to Winslow than anything else.

In fact, if you turn off ’66 and check out the town, you’ll eventually find a few momentos to the song – a statue of a guy standing on a corner, a girl in a flatbed Ford, and a few other song-related gems.

Red Dirt Rangers – Main Street USA

Also known as ‘America’s Main Street’, this little ditty is an ode to Route 66 by Oklahoma staple Red Dirt Rangers.

Holiday Road – Lindsey Buckingham

A soundtrack staple of the classic road trip movie National Lampoon’s Vacation, this Lindsey Buckingham track actually rose to No. 82 on Billboard’s Hot 100 after the film’s release. Heading from Chicago, Illinois to Wally World in California, the Griswold’s obviously graced the mother road from time to time.

Kris Kristofferson – Border Lord

Although the song’s only state reference is Minnesota, Kris Kristofferson was born in Texas before moving on to California, and basically personifies what it means to be an American folk artist on the road.

The Runaways – California Paradise

An LA band singing about California? Seems fitting enough.

Turn up that radio
Hear the rock and roll; Malibu shines like summer gold.
Wild beaches In the salty wind
California summers never end.

Twin Peaks – Under The Pines

I think it’s about time to put something a little more grungy on this playlist. Chicago band Twin Peaks sound like if The Rolling Stones’ classic pop lyrics were hit over the head with a distortion pedal.

Wilco – Via Chicago

Sultry Chicago band musing about their hometown.

But the wind blew me back via Chicago
In the middle of the night
And all without fight
At the crush of veils and starlight

Kanye West, Chris Martin – Homecoming

An obvious ode to Kanye’s hometown; plus it was about time for some hip-hop.

Stevie Nicks – Edge of Seventeen

Making these playlists, it’s always hard to tell where to draw the line between super well-known songs and under the radar gems. Well, this one obviously falls into the former, given relevancy by Nick’s being born in Arizona.

The Kinks – Oklahoma U.S.A.

A little different than the tracks on the list so far, this mellow 1971 ditty from The Kinks album Muswell Hillbillies is a day in the life of an Oklahoma resident.

If life’s for livin’ then what’s livin’ for.

Stevie Ray Vaughan – Texas Flood

The title track from Stevie’s debut studio album, Texas Flood is perfect for driving along Route 66’s Texas portion.

Robert Johnson – Sweet Home Chicago

Sweet Home Chicago is an American classic. Although originally recorded by Robert Johnson in 1936, the song existed long before its studio debut in numerous incarnations, as well as after as a well-covered hit.

Gypsy In Me – Bonnie Raitt

Hailing from California, Bonnie Raitt is an American blues-rock wonder woman. This song is a love-affair to picking up and hitting the open road; a tale as old as time.