Sunday, May 28, 2023


10 great road-tripping roadside America songs

Welcome to the latest installment of Road Trip Playlists.

The United States has long had a love affair with cars and road-tripping, so this week we look at songs that celebrate the great American road trip, and roadside America. In other words, some of the amazing sites and attractions you can find on an American road trip!

As usual, I will try to give a mix of different styles and genres, and a combination of songs you probably already know and love along with some you might not have ever heard before.

Crank up the volume and enjoy this roadside America playlist!

Quick peak at the songs on the Roadside America Road Trip Playlist:

  • See the USA in Your Chevrolet by Dinah Shore
  • I’ve Been Everywhere by Johnny Cash
  • America by Simon and Garfunkel
  • Road Trippin’ by the Red Hot Chili Peppers
  • Route 66 by John Mayer
  • Palisades Park by Freddy Cannon
  • Graceland by Paul Simon
  • Snake Farm by Ray Wylie Hubbard
  • Choctaw Bingo by James McMurtry
  • This Land Is Your Land by Pete Seeger and Company

See the USA in Your Chevrolet by Dinah Shore

In 1953 Dinah Shore was a company spokesperson who introduced the world to the new Chevrolets with this catchy little tune. Why not answer it? After all, America is asking you to call!

I’ve Been Everywhere by Johnny Cash

Johnny Cash’s bouncy fun ode to America is a great U.S. road trip bucket list to aspire to. Johnny’s been EVERYWHERE in this great country (even Chicopee)!

Road Trippin’ by the Red Hot Chili Peppers

The Red Hot Chili Peppers are fully loaded with snacks and supplies and they are inviting you to go and get lost right here in the USA in this beautiful and haunting song.

America by Simon and Garfunkel

Simon and Garfunkel’s soaring harmonies underscore this beautiful song about looking for the soul of America. After having traveled it, though, I can’t imagine counting the cars on the New Jersey turnpike! (For another take on this song, check out this David Bowie cover of it.)

Route 66 by John Mayer

Route 66 is undoubtedly THE most covered travel song in the world. Seems like EVERYONE has a version of this iconic road song. So much so that I have an entire column planned on it in the future. For today, however, let’s motor west and get our kicks to the sounds of John Mayer’s rocking take on the tune.

Palisades Park by Freddy Cannon

This ’50s golden oldie captures the magic of a night at an amusement park, a favorite road trip destination for decades!

Graceland by Paul Simon

Paul Simon has reason to believe we will all be received in Graceland. Join him on his road trip pilgrimage to Memphis in the title track of his masterpiece album.

Snake Farm by Ray Wylie Hubbard

All of us road-trippers have seen roadside reptile farms, regardless of whether or not we have stopped. Ray Wylie Hubbard’s rocking bluesy song captures the essence of the odder and somewhat spookier side of roadside America.

Choctaw Bingo by James McMurtry

FAIR WARNING: Don’t play this one with the kids around!
James McMurtry covers some serious miles in his rocking country storytelling song about one family’s travels to their family reunion. True, some of these family members have questionable morals, but nonetheless they will be having a time at a great big ol’ party like you never saw! A bit of trivia, James is the son of author Larry McMurtry.

This Land is Your Land by Pete Seeger and Company

I will close this Americana playlist with Woody Guthrie’s This Land is Your Land. I chose this particular version of it because it plays ALL the verses of this song that we all sang in grade school. Most people have never heard all the verses. When you do hear them you’ll realize that, rather than the patriotic anthem we usually think of, Woody Guthrie wrote This Land is Your Land as a protest song. It’s as apropos today as ever.

This live recording of the song was part of Kisses Sweeter Than Wine: The Guthrie Legacy Concert in Tarrytown NY, in April 2010. It features Pete Seeger along with Rob Tepper, Work O’ Weavers, The Klezmatics, Fred Hellerman, Nora Guthrie, and Theresa Tova.

What other songs would you add to the Road Tripping Roadside America playlist?  Drop them in the comments below!

Coming next week:

Previously in Cheri’s Road Trip Playlists


Cheri Sicard
Cheri Sicard
Cheri Sicard is the author 8 published books on topics as diverse as US Citizenship to Cannabis Cooking. Cheri grew up in a circus family and has been RVing on and off her entire life.


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1 month ago

WARNING! Choctaw Bingo is not a song to play with kids riding along. Rated R.

Diane McGovern
1 month ago
Reply to  Cheri Sicard

Thanks, Cheri! And thank you for adding the bit about James being Larry McMurtry’s son. I was wondering about that but forgot to look it up when I was done proofing the post. 👍 Have a great day! 😀 –Diane

Diane McGovern
1 month ago
Reply to  Cheri Sicard

Ha! I didn’t listen to it and had never heard of it, so I had no idea! 😆 –Diane

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