Top 10 Travel Songs for Hopeless Wanderers

by Nathan James Thomas

Editor’s note: This is an old entry back from when Intrepid Times was still figuring out who we are, and I was rattling around Europe and America by train and bus — this list has proven popular however, so we’re leaving it up in case any of these songs inspires you on your next adventure. 

Here are my top 10 travel songs for hopeless wanderers – serious travel songs best enjoyed in the company of a stiff drink or on a train late at night (or, ideally, both).

The choices are pretty personal so definitely not a great fit for everyone, but if you’ve got a bit of the old wanderlust in ya you’ll probably discover something here that you’ll like.

10. Wild Country – Chris Whitley

A song about escape which perfectly contrasts the freedom of the open wild with urban drudgery. It’s a song not about traveling but about longing to travel. If it’s been too long since your last adventure, then maybe you can relate.

9. Traveling Alone – Jason Isbell

I traveled from New York to Birmingham, Alabama on Greyhound buses just to see this guy in concert. Hands down my number one musician overall. ‘Traveling Alone” is a haunting tune for anyone whose been on the road for a bit too long. The imagery at the start “mountains rough this time of year…” is incredible.

8. Tangled Up in Blue – Bob Dylan

This tale of misadventure as a man unwittingly pursues his lover across an America now long dead is a great travel anthem. Like most of Dylan’s best songs, you’re never 100% sure what he’s on about, but you feel every word.

7. Turn the Page – Bob Seger

“On a long and lonesome highway, east of Omaha…” with opening lines like that, need I say more? Much prefer Seger’s original, calm version to Metallica’s more aggressive cover.

6. Amtrak Crescent – Scott Miller

The Amtrak Crescent is a train route that runs from New York to New Orleans. When I first heard this song I was taking a slightly trimmed version of the journey, from Birmingham to Washington. Like most great travel songs “Amtrak Crescent” has vivid descriptions of place; “bet it used to be pretty on the Eastern shore… but now it’s more New York down to Baltimore.”

5. Play a Train Song – Todd Snider

A great wee tune about an East Nashville character who was constantly hollering at bands to play him a “train song.” A Kerouc-esque tribute to living in the moment and the adventures of road.

4. Like a Hobo – Charlie Winston

Throwing something a bit more upbeat into the mix. A motivational, jaunty song about the freedom of travel.

3. Fort Worth Blues – Steve Earle

Steve Earle wrote this heartbreaking tribute to his mentor, Townes Van Zandt, shortly after his death. This song is the perfect tribute from one road weary wanderer to another.

You always said the highway was your home,
but we both know that that ain’t true.
It’s just the only place a man can go,
when he don’t know where he’s traveling to.”

2. Waiting ‘Round to Die – Townes Van Zandt

Possibly one of the finest poets of 20th century America, certainly one of the all time great songwriters. Waiting Around to Die was Towne’s first original song, and it’s a chilling, haunting description of the salvation and dangers of life on the road.

 1. Wicked Twisted Road – Reckless Kelly

“My first love was the wicked twisted road,
I hit the million mile mark at 17 years old
Never saw the rainbow, much less the pot of gold
Yeah my first love was the wicked twisted road”

A deeply felt, beautiful song that every true traveler will feel was written especially for them.

Let me know what I’ve missed!
Happy wanderings
Nathan Thomas

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