More than they do for any other season, music fans love to make fall playlists. The autumn months are a time to unpack our flannel and stock up on pumpkin purée before it’s sold out while arguing over which Nick Drake song sounds best in 57-degree weather. It’s also an opportunity to listen to songs that make us feel warm and cozy, as we nod in agreement that Fleet Foxes do indeed sound perfect right now. From porch ballads to harvest jams, here are 13 songs for the fall season.
Bob Dylan, “Caribbean Wind (rehearsal with pedal steel)”
One of the many treasures on 2017’s Trouble No More, the thirteenth volume of Dylan’s Bootleg Series. An outtake from Shot of Love, “Caribbean Wind” originally appeared on the 1985 box set Biograph, but this rehearsal take offers a slightly different version. It’s stripped-back and intimate, as Dylan sings about a lost love shrouded in mystery. Oh, and he mentions playing a show in Miami — where we all want to be when it starts to get chilly.
The Byrds, “Hickory Wind”
In continuation with songs about the wind, here’s one from the Byrds’ country-rock masterpiece Sweetheart of the Rodeo. Although a bulk of this album pairs well with a summer barbecue, Gram Parsons’ lines about the wind being a feeling gives the song an autumnal vibe, his vocals melting across a pedal steel guitar. Next stop: Parson’s final solo LP, Grievous Angel.
Paul McCartney, “Man We Was Lonely”
This fall is also the waiting period for McCartney III, which arrives in December. In honor of the Macca album trilogy, here’s “Man We Was Lonely,” the final track on Side One of 1970’s McCartney. Paul and Linda used to ride on fast city lines, but now they’re home — like most of us are. Similar to “Junk,” it’s a song steeped in fall comfort, best played when eating pumpkin pie in wool socks.
There’s something about Julien Baker’s voice that tugs on your heartstrings, especially when she kicks a song off by describing a $20 dreamcatcher that hasn’t done its job. Wait for her to harmonize with bandmates Phoebe Bridgers and Lucy Dacus, and an autumnal chill will creep down your spine.
Emmylou Harris, “Easy From Now On”
Harris’ 1978 album Quarter Moon in a Ten Cent Town was practically made for autumn, down to its artwork of an open road under a purple evening sky. This gorgeous opening track is great for a midnight drive, or sitting out on your porch in a rocking chair. I don’t own a car or a porch, but both sound pretty dreamy.
Fleet Foxes, “Ragged Wood”
Fleet Foxes are the quintessential fall band, most recently dropping their new album in sync with the autumnal equinox. This song, from their 2008 self-titled debut, contains imagery of mountains, fire, forests, and sparrows — you don’t need more convincing than that.
Taylor Swift, “Cardigan”
Don’t worry: I haven’t forgotten Folklore. From black lipstick to that tattered cardigan, this track is peak fall, as Swift likens herself to one of the most hip clothing items of all time. One could argue that “All Too Well” would fit better here, but keeping scarves in drawers is so 2012.
Neil Young, “From Hank to Hendrix”
This year’s harvest moon has already passed, but the album of the same name is perfect year-round. Button up your flannel for “From Hank to Hendrix,” a stunning classic in which Young studies a relationship in peril. James Taylor and Linda Ronstadt provide backing vocals, while Young tears through the harmonica and sings about getting a divorce, California-style.
Love, “Always See Your Face”
A cozy heartbreaker that John Cusack sulks to in High Fidelity. The final track to 1969’s Four Sail is arguably one of the band’s greatest achievements, as Arthur Lee begs to be put out of his misery — to the extent that he’s screaming in the final seconds, his vocals burning with fury and devastation. It’s a song worth playing on repeat, but then again, there’s always Forever Changes.
Nick Drake, “From the Morning”
Drake didn’t live to see Pink Moon become a classic, an album that ranks high on best-ever lists and appears on playlists with themes similar to this one. The 1972 album’s final track, “From the Morning,” is hopeful and sparse, like clouds parting on a crisp fall day. The song’s best lines — “And now we rise/We are everywhere” — are even inscribed on his tombstone.
Paul Simon, “Duncan”
The cover of Simon’s self-titled solo album features the songwriter in a furry hooded jacket, and basically every song contained within is fitting for fall. On “Duncan,” he plays the acoustic guitar and tells the epic tale of a young man who departs for “sweet New England” and embarks on an adventure.
Tom Petty and the Heartbreakers, “Southern Accents (Live)”
The title track to Petty and the Heartbreakers’ 1985 album may not have any lines about autumn in it, but this live version carries the emotional gravitas desperately needed this season. Taken from a Gainesville, Florida show in 2006, it’s perhaps the greatest performance of Petty’s career, where he sings about his hometown as he’s standing in it. As he grips the microphone and closes his eyes, it’s a heavy thing to witness, even more so now that he’s gone.
Carly Simon, “Coming Around Again/Itsy Bitsy Spider”
Eighties Carly is extremely underrated. The best place to start is this 1987 performance of “Coming Around Again,” taken from Live from Martha’s Vineyard. Simon belts through the track at sunset, the wind blowing through her hair as she sings about a crumbling marriage (toasters are repaired, yet soufflés are burned). Things get weird when she recruits several children in sweaters up on stage to sing “Itsy Bitsy Spider,” providing a lovely Halloween touch.