Sing Your Way Across America’s Midwestern Plains

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Not many musicians sing about the Midwest. Maybe because Sioux City’s grain silos aren’t quite as dramatic New York City’s skyscrapers. And, falling in love on a summer beach sounds way more romantic than falling in love in a snowy field of corn. Or, sand dunes in the middle of the plains in Nebraska or Kansas or Wisconsin. 

That said, the natural beauty of the Midwest is nothing short of magical. Its silence is captivating and mesmerizing and its skies dramatic and full. And, a road trip is the best way to see it.

Dunes in Nebraska (photo credit

Or possibly just because there’s something indescribable about America’s middle section – something too vast and under-stated to put into lyrics.

But that’s just one more reason to try. So dig out the ol’ paper map, spread it over your steering wheel and wander in whichever direction you choose. From the shores of The Great Lakes to the rutted soil of the Great Plains, there’s enough space out here to road trip the entire summer, and never get bored.

Midwest summer road trip travel playlist

Want a great play list for your road trip? These songs are sure to put you in the right mood.

Sprawl II – Arcade Fire – It might seem strange to start a travel playlist involving some of the country’s flattest land (cough cough Kansas) with a song about mountains. But we’re talking an escape from towering cities – for the promise of empty horizons.

Flyover States – Jason Aldean – A  well-deserved tribute to the space you only see from an airplane window. “They’d understand why God made these flyover states.” You tell ‘em, Jason!

Another Traveling Song – Bright Eyes – Former Bright Eyes singer/songwriter, Conor Oberst, hails from Nebraska. When he describes “all the billion highways at the break of dawn,” he could very well be vocalizing his home state, where manic interstates give way to sunrises over boundless prairie.

Back Where It All Begins Allman Brothers – Classic rock guitar jams are made for road trips. And if you ask me, “Get out on the highway and just let it roll on” should be the mantra for any region that takes 18+ hours to drive across.

Small Town – John Mellencamp – Indiana-born JCM is a bit of a Midwestern troubadour, telling musical stories about his birth-land. This version of a small-town upbringing may not sound too glamorous, but it has it’s secret charms.

Backroad Song – Granger Smith – Off the beaten path is an easy concept in these parts; you’re out of the mainstream the moment you hit southwest Ohio. Make the most of two-lane highways and gravel tracks, windows down, where “the breeze smells like a summertime hay field’s just been cut.”

Midwest Sky – Augustana – Unfortunately, this song isn’t on Spotify; but if you find the YouTube version, close your eyes and picture the cloud shadows that will race your car “underneath this Midwest sky…”

 You & I – Lady Gaga – Rumor had it there was a man behind this song. So when Lady G sings “Something about this place…”she might be thinking of a romantic interest, not just fields of rolling wheat. Either way, it’s still (sort of) a love song to Nebraska.

Kansas City – Dylan/Mumford & Sons – Bob Dylan never recorded a tune with these lost lyrics; then 2014, Mumford & Sons were asked to give it a try. The folksy result sounds just like a love song to a long summer’s drive.

Motorcycle Drive By – Third Eye Blind – One of the best parts of a Midwest road trip is the ownership that all this emptiness gives you. “And I’ve never been so alone / I’ve never felt so alive.”

When I Die – The Waifs – While the region’s tiny communities may feel stifling, there’s something to be said for those places where everyone knows your name, and the rudest thing you can do is not return a “hello.” Who wouldn’t want to spend eternity here?

My Church – Maren Morris – Contrary to common misconception, the Midwest is not the Bible Belt. It does, however give you a healthy understand of life, death, and the contentment found in between. “I just keep the wheels rolling, radio scrolling / till my sins wash away.”

Dakota – Stereophonics – “I don’t know where we are going now…” It’s the ultimate Great Plains statement: 360 degrees of freedom to move in, onward and outward. Good luck, good travels.

Which songs are on your Midwest travel playlist?  Here are ten more great ones for your list.


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