Who can resist the sounds of autumn? Leaves crunching underfoot, whispering winds gusting through half-naked trees, the sharp cracks and hisses of an evening bonfire, and the dulcet tones of Taylor Swift. It’s undeniable that certain songs resonate deeper with us during specific times of the year, and, for whatever reason, large parts of Taylor’s discography tend to cut deeper (in a good way) during the fall season. I know that not all of Taylor’s music is “autumn music”—don't worry, I’m not trying to convince you that Cruel Summer or 22 are fall songs. I also understand that associating songs with seasons is very subjective. Honestly, 99% of it can probably be attributed to where and when we heard the song first. However, I maintain that there are specific criteria for classifying "autumn songs" and that large parts of Taylor's discography fit within that criterion.
And what are those criteria? I’m glad you asked. I considered three principles in crafting my list.
1. Subject Matter
Autumn in itself is a journey, transporting us from warm summer days to the bitter beginnings of winter. I want that same sense of experience in an autumn song. Living life to its fullest, even if failing in the process. I’m looking for introspection, pain, longing, and reminiscing—but it doesn’t have to be all doom and gloom. Autumn can also be a time for new beginnings and embracing change. Bonus points if the song has any sort of lyrical reference to autumn in it.
2. Instrumentation
The music genre I associate most with autumn—aside from horror movie soundtracks—is folk. The pairing of acoustic guitar and ethereal vocals strikes me as perfect for an autumn hike. That’s not to say that my list will end up being the top twenty Taylor Swift folk songs—but I’m looking for songs with similar instrumentation. Guitar, piano, vocals—the simpler and rawer the better. What hurt the ranking of a lot of songs was any instrumentation markedly “not autumn”. For example, not that it would have been on the list otherwise, but the chimes in Wonderland make it a distinctly winter song.
3. Atmosphere
This is where the innate feeling of a fall song comes into play. Several songs may fit the above criteria but just don’t feel like an autumn song. I imagine this playlist to be listened to while walking through a forest on a brisk October afternoon, enraptured by bursts of red, orange, and yellow foliage. A poignant reminder of past pain but also inspiring excitement for what the future brings. There are songs on this list that don’t necessarily fit that description—autumn as a season prompts a variety of moods—but that’s the overall vibe I’m going for.
With Red (Taylor’s Version) on the precipice of release, the time is ripe to revisit all of Taylor’s past autumn glories. Without further ado, here are my top twenty Taylor Swift songs for autumn. Follow me on Spotify at "First Frost Josh" for more autumn themed playlists and music recommends!
1. All Too Well
This is the one entry on the list that I’m confident people won’t be angry about. What can I say about All Too Well that hasn’t already been said—the Autumn imagery; the soft guitar that descends into yelling heartbroken strums; the pain of trying to move on as the past clings to you like a wet t-shirt. It’s the elitest of elite sad autumn hike songs.
2. Safe and Sound
For me, it’s the rawness. The simplicity of the lyrics. The arpeggiated guitar verses. Taylor’s breathy vocals. It all combines so well to create the perfect soundtrack for a gloomy autumn hike. The song gives off a unique cabincore vibe that we don’t really see from Taylor again until maybe folklore and definitely evermore. Safe and Sound is about seeking refuge against the seeming inevitability of darkness. A plaintive yet hopeful lullaby.
3. Haunted
The Halloween-appropriate title isn’t all that makes this song autumnal. Its opening strings and electric guitar are reminiscent of a horror movie, imbuing the song with an intensity that matches its message. I love the transition from the opening's pulsing violence to soft, jittery piano overlaid with Taylor’s voice. Haunted is a reminder that things can change in an instant. A reminder that the dread and horror we feel when the rug is pulled out from under us is hard to shake, even when we see it coming
4. Back to December
A lot of people forget that the season only changes on the 21st—December is actually more autumn than winter. Back to December is like Haunted in that it bleeds passion and intensity; you can hear Taylor’s voice dripping with nostalgia and regret. The song intimates that it may be too late to change things, but also that despite logic, you should try anyways. That feverish feeling of living— putting yourself completely and utterly out there—is my favourite part of this song. There’s a reason that “But this is me swallowing my pride / Standing in front of you, saying I'm sorry for that night” hits so deep every time.
5. Eyes Open
I’m curious how people will react to Eyes Open being this high on the list. A deep cut from The Hunger Games soundtrack, it’s not a song casual fans would associate with Taylor—hell, at least Safe and Sound got a music video. Eyes Open is one of my Grade-10 October cross-country-meet songs, so it holds a special place in my heart. The song is isolating in an empowering way, asserting that you have what it takes to soldier through whatever stands in your way. The rock instrumentation gives the track an edge that transforms its melancholic air into one of liberating indignation.
6. Cornelia Street
Cornelia Street deals with a different kind of struggle than the preceding songs: the fear of losing what you have. The song is an appreciation of the journey. It's a recognition of how far one has come and how afraid they are of regressing into what they once were. Taylor’s vocals are on full display in this song. Her smooth accentuations shift to breathy confessions and back again, assisted by a pulsating beat that switches on and off, ushering the listener through the track. And, of course, I would be remiss if I didn’t mention my favourite lyric: “Windows flung right open, autumn air / Jacket 'round my shoulders is yours”.
7. Sparks Fly
Sparks Fly is spontaneity. If I were to choose one of Taylor’s songs to embody my autumn-ascribed tenet of opportunity and living life to the fullest, Sparks Fly would be it. The song is teeming with passionate longing, making it the perfect material for spirited brooding or typical heart-eyed daydreams. I mean, who doesn’t dream of being kissed in a pouring autumn rain?
8. Cardigan
If Sparks Fly is spontaneity, then Cardigan is nostalgia. The muted instrumentation is haunting; I feel as if the song is whispering secrets to me between lyrics. That ghostly aura speaks to the song’s feeling of loss, the “what could’ve been”. However, I find the track to be more bittersweet than sad. Time and reflection have dulled past highs and lows into a sentimental truth—a process illustrative of the introspective allure of fall.
9. Teardrops on My Guitar
10. White Horse
11. Tim McGraw
12. Last Kiss
If you’re listening to this playlist in order, get ready to be emotionally devastated! The four songs share several similarities: the trademark acoustic guitar of "country Taylor", agonizingly wistful heartbreak, and a relatability rooted in youthful vulnerability. Taylor’s ability to transport the listener to a different time and place is part of what makes her music so enchanting. At the end of the day, the “autumn atmosphere” is a form of escapism, and these songs do their job in allowing you to immerse yourself in someone else’s story. A quartet of elite sad boy (or girl or person) autumn hike songs fit to join All Too Well.
13. Begin Again
A change of pace from the heart-wrenching ballads above, Begin Again preaches renewal. The silky guitar and delicate vocals embody the tremulous optimism of someone trying to be themself again. The newness of fall, with its steadily declining temperature and the changing colour of falling leaves, promotes change and fresh starts. This is the niche that Begin Again satisfies, the perfect song for first dates at the pumpkin patch or apple orchard.
14. You Belong With Me
15. Fifteen
16. The Best Day
Continuing the upbeat vibes of Begin Again, we have a trio of songs from Taylor’s second album, Fearless. I had trouble placing Fearless songs on this list. To me, there’s a marked difference between summer country music and autumn country music. Summer country songs, you heedlessly scream out the car window with your friends. Autumn country songs have a bit more emotion behind them; they’re the songs you sing alone, dramatically shouting from your knees. The three songs above cover intimately familiar themes: an unrequited crush, the growing pains of youth, and the warm glow of familial love. They’re perfect both for reminiscing and dreaming excitedly about your future.
17. Look What You Made Me Do
Time for a massive tonal shift! So far, we’ve looked at songs that evoke passion—extreme emotion—but Look What You Made Me Do, albeit teeming with anger and resentment, is just an fun song. The opening is undeniably creepy, with lilting piano-synth and strings abruptly crashing into the staccato beat that dominates the rest of the track. The music video alone makes Look What You Made Me Do a worthy inclusion on this list—zombie Taylor anyone?
18. Come Back… Be Here
19. Dear John
Switching back to our regularly scheduled heartbreak, Come Back… Be Here and Dear John are two of Taylor’s most acutely painful songs. There’s an excruciating similarity in how Taylor stretches out specific syllables in both songs, culminating in the throaty yell of the titular phrase in each chorus. The songs are slightly lacking in autumn atmosphere, but the strumming acoustic guitar and poignant lyricism get the job done and then some.
20. Out of the Woods
In the vein of Haunted’s distinctly autumn title, how could I have a Taylor Swift fall playlist without including Out of the Woods? What strikes me about Out of the Woods is its sense of urgency. Sharp drumbeats pulse throughout, contributing to the feeling of omnipresent struggle that builds as the song presses on. This list’s first entry from 1989 (which I generally consider too poppy for autumn listening), Out of the Woods’ explosive, ranting bridge seals its entry on this playlist.
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