Sunday, May 28, 2023


Road Trip Play Lists: 8 awesome life on the road songs

Welcome to our second installment of Road Trip Playlists (check out the first installment, “Joyous Songs to Start Your Journey,” here).

This week I wanted to focus on songs about the lifestyle of living on the road and experiences that can happen out on the open road.

As always, I tried to mix it up with different genres and songs you know with those you likely never heard before. Although I will put in the disclaimer that this week’s playlist is a little bit heavy on the country side. It just worked out that way with this general topic.

This week’s road trip playlist quick peak at the songs:

  • Big Log by Robert Plant
  • Convoy by C. W. McCall
  • East Bound and Down by Jerry Reed
  • I Can’t Drive 55 by Sammy Hagar
  • Big Joe and Phantom 309 by Tom Waits
  • Dead Skunk by Loudon Wainwright III
  • The Load Out/Stay by Jackson Browne
  • I’m On My Way by Rhiannon Giddens with Francesco Turrisi

Big Log by Robert Plant

Robert Plant’s haunting Big Log is my personal all-time favorite road song and has been since it came out in the ’80s. For me, it personifies driving beautiful but lonely highways while still being compelled to keep on. My love is definitely in league with the freeways and the coming of night. And there is no turning back!

Convoy by C.W. McCall

This song charted in the middle of America’s brief 1970s CB Radio craze, but it is still a fun, albeit kitschy, tune to put on your road trip playlist. Plus, I love truckers and have always found them most helpful and amenable in my RV travels. In my opinion, there’s no safer way to travel down the highway than in the middle of a welcoming truck convoy!

East Bound and Down by Jerry Reed

A great follow-up to Convoy is Jerry Reed’s East Bound and Down from the Smokey and the Bandit movie soundtrack. This lively country ditty will be sure to have everyone singing along, especially if you have a long way to go and a short time to get there!

I Can’t Drive 55 by Sammy Hagar

Supposedly this hard-rocking road song was inspired by a real event when Sammy got pulled over for speeding and thought to himself, “I can’t drive 55.” Sammy’s frustration is one we have all felt. Even though, judging from the comments on this post, I know almost all of you keep your traveling speeds safe.

Big Joe and Phantom 309 by Tom Waits

Tom Waits is at his storytelling best in this eerie song about a weary hitchhiker who gets picked up by what turns out to be a ghost trucker. This is an awesome moody track that, regardless of whether or not you believe in ghosts, evokes the emotions of lonely road life.

Dead Skunk by Loudon Wainwright III

Yes indeed, there is even a song about road kill! Loudon Wainwright III’s whimsical song details something all road trippers have experienced, a dead skunk in the middle of the road stinking to high heaven! The kids will especially delight in singing along with this tune, and will likely start up again whenever you pass one of the unfortunate deceased creatures.

The Load Out/Stay by Jackson Browne

Sometimes when living on the road you just want to stay a little longer before packing it all up. Jackson Browne’s classic song, featuring the late, great David Lindley on falsetto vocals for Stay, is written from the perspective of a traveling rock star. Nonetheless, it evokes emotions all road-trippers can relate to at one time or another. It’s also interesting to note how much road-tripping has changed since the song came out in 1977. Browne and his entourage traveled in high style back then, with “8-tracks, and cassettes, and stereo” on the bus!

I’m On My Way by Rhiannon Giddens with Francesco Turrisi

I’d like to dedicate this song to the full-timers (or most-timers) who, like me, plan very loosely at best. “I don’t know where I’m going but I am on my way.” A hauntingly beautiful modern folk music track, you’d be hard-pressed to find a clearer, purer voice than the incredibly talented Rhiannon Giddens. Even discounting her amazing vocals, the soul-tugging, emotionally charged music accompanying them make this song unforgettable.

Coming next time: “Born to roam” road trip playlist

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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Jamie e
1 month ago

You can add Jackson Browne anytime! The go-to perennial wheels-on-the-road guy. We’re the same age with a lot of shared running-down-the-road/running-on-empty decades-old memories!

Neal Davis
1 month ago

Thank you, Cheri! I recall “Dead Skunk” was released and popular when I was in my early teens. Probably because it is associated with a special time of my life, I really enjoy the song still. DW, almost 9 years my junior, cannot stand it. So I listen when I can without her overhearing.
PS, When we left for Alaska in 2019, anticipating an early September return, I found and played “See You in September” by The Happenings to our house the last few days before we left. 🙂 😎

Steve H
1 month ago

My go-to is “Two Lane Highway” by Pure Prairie League, especially when Vince Gill is singing lead.

1 month ago

Keep up the songs! Loving some of these I’ve never heard (well a couple!) Keep on truckin!

1 month ago

Wow, thanks for the introduction to Rhiannon Giddons. What a voice.

1 month ago
Reply to  Betty

Rhiannon Giddons is amazing. I love her voice and have followed her for a long time. Search on YouTube for Rhiannon Giddons/Paul Simon. There is a great video of her singing a Paul Simon song – wish I could remember the name – with him accompanying her on guitar. It is a live performance at a festival back east and sort of “unscripted”. She also sings with the Carolina Chocolate Drops.

Diane McGovern
1 month ago
Reply to  Janet

Isn’t Rhiannon amazing? I had never heard of her before I saw her on Cheri’s list of “life on the road” songs. Wow! Here’s a link to a YouTube video that someone shot off the TV of Rhiannon and Paul Simon, but it’s better than nothing: (Another one I tried to watch of this performance was skipping, so went with this one instead.) Also, to learn more about this very accomplished and incredible woman, read this: Have a great day, Janet. 😀 –Diane at

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