While it seems counterintuitive to embrace the cool when ensconced in the steamy south, the relentless humidity has given us an appreciation for crisp air and autumnal road trips like nothing else. We’ve been chummy with Max Wastler since we first discovered his tartan-loving blog, All Plaid Out a few years ago and were instantly attracted to his down-home yet urbane approach to Americana culture and travel. His taste in music rivals his taste in pie, and his dispatches from the Windy City make us want to book a long weekend to Chicago tout de suite, despite its frigid reputation. In honor of apple pie, long drives at dusk, and well-worn flannels, we present Max Wastler’s soulful and nostalgia-tinged October road trip. Stream the playlist, engineered for hours spent behind the steering wheel, over on Spotify or listen below.
I grew up on Route 66. No, really. In 2005, Missouri named the road along the backside of my parents’ neighborhood in St Louis a state scenic byway. You can now drive that road from Illinois to Kansas. With past experiences as a traveling salesman and today as I crisscross the U.S. to meet the artists, artisans, and craftspeople who are still making things in their backyards, I often find myself retracing the old haunts along the Mother Road. What I’ve found most fascinating is how this historic byway continues to inspire and instill a true sense of pride of place especially in those of us lucky enough to have called this road our home.
Woody Guthrie – This Land is Your Land
Mr. Guthrie was born in Okemah, Oklahoma, just South of Tulsa. As the forebear to such wonderful singers and songwriters as Pete Seeger, Bob Dylan, and Bruce Springsteen, it’s only appropriate we start out with his Anthem of America’s open road.
Muddy Waters – I’m Your Hoochie Coochie Man
I can’t turn the corner at Jefferson and Jackson Boulevards in my hometown of Chicago without hoping I might catch sight of a big, old jalopy, packed with everything but the kitchen sink, looking like something out of a Steinbeck novel, parked out front of Lou Mitchell’s, the best breakfast in the city (complete with a free box of Milk Duds for the ladies), and get this: It’s the start of Route 66. The city of Chicago was once synonymous with the blues, and no one more perfectly exemplified the Chicago Blues than Mr. Waters.
Nat King Cole – Route 66
No Route 66 playlist would be complete without this classic rendition of Bobby Troup’s song, the swingin’est tribute to the highway that “winds from Chicago to L.A.” and deep into the fabric of America.
Chuck Berry – Nadine
“I saw her when she turned and doubled back and started walkin’ toward a coffee-colored Cadillac. I was pushin’ through the crowd to get to where she’s at, and I was campaign shouting like a Southern diplomat.” There’s a reason they call him the Shakespeare of St. Louis. And that’s not even the best line in the song. This could be a playlist comprised solely of Chuck Berry tunes, and you’d have enough musical fuel to get you to the Pacific and halfway back.
Son Volt – Windfall
Mr. Jay Farrar, co-founder of seminal alt-country group Uncle Tupelo, is a native of Belleville, Illinois, a last stop in Illinois before crossing the Mighty Mississippi into the Show-Me State, Missouri. This track should be the theme song of road-weary travelers the world over.
J.J. Cale – Hey Baby
Having penned the classic Clapton songs “Cocaine” and “After Midnight,” Tulsa native J.J. Cale is undoubtedly a songwriting legend, but with hits like “Crazy Mama” and this classic, he’s a force in his own right. Cale’s pace is perfect for a casual drive down the rubbled remains of Route 66.
See more of Max Wastler on the road over on his Instagram feed.