Road trips always have been a huge part of my life.
Before I got my license, I traveled with Mom & Dad, folded like a lawn chair into the back seat of their Oldsmobile Calais. Immediately after college, I used my Plymouth Voyager minivan to schlep from Boston to New York to chase down a long-distance girlfriend.
In more recent years, I’ve slogged my way all over the West in my Nissan X-Terra, chasing down stories and people and dreams.
On all these trips, one thing has remained constant: I pass time by singing.
I’m not talking quiet humming here; I’m talking American Idol-style, feel-it-in-your diaphragm, belt-it-out blaring. I’m the guy you see flying by in the left lane, so deeply engrossed in song that I don’t even realize you and your buddies are making fun.
Naturally, then, the top ten songs on my all-time road-trip playlist are (almost) all about faraway places, or the processs of getting from here to there; wherever “there” might be. The songs also share another trait: they’re all kick-ass sing-alongs. Pardon the pun, people, but that’s how I roll.
Freedom of the Road (Martin Sexton): I could sing (and have sung) this folk ditty at the top of my lungs cruising across I-15 at 90 mph. The high notes in the bridge really need some good breath support, but if you’re road tripping solo, nobody will know if you can’t quite get ‘em. Beside, how could any road-tripper not sympathize with lyrics like these: “There’ll be no more pay-per movies/from those economy motels/No more trash in the back seat/from Mickey D’s or Taco Bell.”
Closer to Fine (Indigo Girls): Hands down, this puppy boasts the best harmonies since Simon & Garfunkel, which is reason enough to put it on the list. The song is about a journey toward self-improvement; a road trip of the soul. I usually alternate parts—on trips north I sing along with Amy; on trips south I sing along with Emily. Just don’t ask my wife how she feels about my falsetto.
Born to Run (Bruce Springsteen): Pretty much anything from Springsteeen (except maybe the Tunnel of Love record) could qualify for this list, but BTR is the Boss at his upbeat best. Air-drumming on the steering wheel is a must when you listen to this puppy; just look out for aggravating that carpal tunnel.
Pineola (Lucinda Williams): Every road trip needs some sorrow, and that’s where this “destination ballad” from Lucinda comes in. (As an aside, most of Lucinda’s new stuff is too happy for me now.)
American Tune (Paul Simon): Not to be confused with “America” by Simon & Garfunkel (which is one of the all-time classic travel and road-tripping songs; see Jenna’s list), this was one of Simon’s best solo projects. Sweet lyrics + simple melodies = carefree driving for hours.
The Thing About Love (Alicia Keys): Alicia’s fast stuff can be a bit melodramatic (as can she), but this slow song about the places love takes us is the perfect key for belting. I’m not sure I’ve ever listened to this song just once—usually end up playing it three or four times in succession. I admit it: I have a wicked crush on her.
Memphis (Cliff Eberhardt): Keeping it slow, this is arguably one of the best and most underappreciated travel songs ever written. Instead of focusing on the benefits of travel (which, of course, we love to do here at Flyover America), Eberhardt croons about the hardships of being on the road away from his lover. Another perfect sing-along, especially if your enamorada isn’t sitting in the passenger seat. There’s also a great version of this song by Cry Cry Cry.
The Next Best Western (Richard Shindell): Obscure? Perhaps. But this folk anthem is perfect for that time of night when, well, when you’re looking for the next hotel with a vacant room. Also, I always feel like a bit of trucker on long road trips, and love how Shindell speaks directly to that sensation: “Whoever watches over all these truckers/Show a little mercy for a weary sinner/And deliver me, Lord deliver me/Deliver me to the next Best Western.”
Send Me on My Way (Rusted Root): The band no longer exists in its original coupling, but hands down, there is no greater party song. The tune is great in particular for road trips with friends. Best part: imitating that whistle/Glockenspiel thing.
Fix You (Coldplay): Few choruses invite sing-along as effortlessly as the one in this song. The “journey” in this song is metaphysical (ie, going from broken to fixed). It also makes me think of this British guy with whom my wife and I hiked the Inca Trail. He had made a special playlist for the second day, and timed it perfectly so the chorus of this song was playing as we reached Dead Woman’s Pass.
Doreen (Old 97s): So this isn’t really travel-related at all, but it’s a fun song with a light-hearted twang and a great sing-along chorus. When you’ve got nothing but highway in either direction, who could ask for anything more?
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