10 of the Best Wisconsin Road Trip Songs

Avoid those awkward silences with this selection of Wisconsin road trip songs.

Road trips are the best, but the one thing they require more than anything is music. If you’re alone, God forbid you get stuck with your thoughts for longer than five minutes. And if you have company, are you really going to be able to sustain a conversation for more than thirty minutes? Avoid those awkward silences with this selection of Wisconsin road trip songs.

1) “The Wreck of the Edmund Fitzgerald” by Gordon Lightfoot

A ballad of a famous Lake Michigan tragedy, this song has just the right vibe for driving along a long highway. Wisconsin gets a mention in the lyrics, which paint a vivid picture of the wreck.

2) “Jungle Love” by Steve Miller Band

Good ol’ Steve Miller, a proud son of Milwaukee, rocks out on this track. It’s got some psychedelic beats and all that 1977 energy stored within, just primed for a ceiling-smacking sing-a-long.

3) “Comin’ Round to Get You” by Farewell Milwaukee

Farewell Milwaukee is a band from … Minneapolis. But still, they get Midwestern credit, and we appreciate the name. This is a nice dose of modern folksy tuneage to gas up the musical tank. This song is especially fitting for the early evening hours, when the sun is setting and the driving gets quiet.

4) “22 (OVER S∞∞N)” by Bon Iver

You know there couldn’t be a list of Wisconsin road trip songs without Justin Vernon, the crown prince of modern Wisconsin music. While his first album as Bon Iver has some obvious picks (“Skinny Love,” “For Emma,” “Wisconsin”), this choice comes from his latest, and by far most experimental album 22, A Million. The song opens with a looped sample of Vernon’s heavily-pitched vocals and builds layers on his distinct falsetto. Just as it opens the album, this song will open your road trip with a nice dose of melancholic hopefulness.

5) “Turntable” by Dead Horses

This Milwaukee band released a new album in April, and it’s receiving loads of attention and glowing reviews. It tells the story of lead singer Sarah Vos, whose family was expelled from the fundamentalist Wisconsin church where her father served as pastor, when she was fifteen. This is some of the best local music out there right now and will absolutely enliven any trip.

6) “Once in a Lifetime” by Talking Heads

Feel trapped in a rote suburban existence of luxury SUVs and steady income, gradually revealed to be a self-inflicted hell of creeping insanity and deep dissatisfaction? It’s Talking Heads time. Not only is this a great song by a great band — it’s a homegrown hit. Talking Heads guitarist/keyboardist Jerry Harrison was born and bred in Milwaukee.

7) “Revival (Interlude)” by Eminem (feat. Alice and the Glass Lake)

In the middle of a really aggressive rap album by one of the genre’s profane kings, this beautiful, sad song by the late Wisconsin singer-songwriter Alicia Lemke pops up. Lemke was born in Madison and performed as Alice and the Glass Lake, before dying of leukemia at age 28. These 51 seconds are legitimately amazing and serve as a perfect, if unexpected, gateway to Lemke’s music. After this song, you should definitely add Lemke’s posthumous album Chimaera to your playlist.

8) “River in the Pines” by The Deep, Dark Woods

This tragic folk song set in “Wisconsin’s dreary clime” was originally sung by Joan Baez, but this Canadian Band’s version brings a new energy to the song — so much so that you might not realize it’s about a guy dying in a river accident and leaving his new wife widowed. It’s also a worthy introduction to another of their fantastic songs, “The Place I Left Behind.”

9) “Cleopatra” by The Lumineers

Personally, I prefer the song “Sleep on the Floor” from the Lumineers’ second album, but the music video for “Cleopatra” was partly filmed in Milwaukee, right outside Discovery World, so it deserves credit for the local connection. The Lumineers are masters of the knee-slapping, floor-stomping road trip song, making “Cleopatra” a perfect addition to your playlist.

10) “Welcome Home, Son” by Radical Face

This song is radical. The crescendo at two minutes and twenty-two seconds marks the exact thematic point to end a road trip, as you pull back into your driveway, sigh and step out into the rest of your life.



Archer is the managing editor at Milwaukee Magazine. Some say he is a great warrior and prophet, a man of boundless sight in a world gone blind, a denizen of truth and goodness, a beacon of hope shining bright in this dark world. Others say he smells like cheese.