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Fall is here, which means it’s officially time to blast “Sweater Weather” by The Neighbourhood. Here are 15 songs spanning five decades to add to that driving-to-see-fall-leaves playlist!

“The Circle Game” – Joni Mitchell (1966)

“Then the child moved ten times ‘round the seasons, skated over ten clear frozen streams”

Fall is the perfect time to recognize how wizened you’ve become and partake in some self-reflection as summer draws to a close. In this song, Mitchell allows listeners a glimpse into the life of a child quickly growing up amidst dragonflies and stormy skies. Though it can feel scary, there is something beautiful about the emphasis Mitchell places on the cyclical nature of human existence.

“Cracker Jack” – Dolly Parton (1973)

“Through the woods and fields we would often roam about”

This is both a lighthearted and heart-wrenching song about Dolly coming across a lost puppy and taking care of him until he grows old and passes away. It’s a timeless country song that evokes strong childhood nostalgia for pet owners and brilliantly incorporates the start and end to a cycle of life without leaving listeners feeling too sad.

“The Moon’s A Harsh Mistress” – Glen Campbell (1974)

“The moon, a phantom, rose, through the mountains and the pines”

In this song, the speaker likens his lover to the moon, enchanted by her beauty and saddened by her nomadic ways. This is a poignant, poetic story of heartbreak that weaves in the perfect amount of eerie imagery to classify it as a “fall song.” 

“Landslide” – Stevie Nicks (1975)

“Can I handle the seasons of my life?”

This song is similar to “The Circle Game” in the way that they are both simply about growing older. So many different interpretations have been assigned to this masterpiece, and I almost feel that commenting on its meaning would be futile. 

“Southern Accents” – Tom Petty and the Heartbreakers (1985)

“Think I might go work Orlando, if them orange groves don’t freeze”

Petty sings about the perpetual and beautiful traces of where you come from in everything you do. It’s a simple song, and reminds me of permanent things moving slowly through temporary changes, like the leaves changing color in the fall and returning green in the spring.

“Look Up” – Toni Collette & The Finish (2006)

“The sky is falling, colors changing, people laughing”

In the first half, Collette touches on serious topics like climate change and natural disasters but transitions into admiration of “lovers swaying” and a “town that’s praying” to reiterate how cyclical life is, similar to Joni Mitchell. She uses a lighthearted and playful composition to highlight hope above all else.

“All Too Well” – Taylor Swift (2012)

“Autumn leaves falling down like pieces into place”

The Red album embodies fall so well as a holistic composition, so it was difficult to choose only one song from it. In “All Too Well”, Swift reminisces on a relationship that was characterized by long drives, cold air, photo albums, and a scarf kept in a drawer. Though the loss of such a good period in her life is hard to hear her navigate, few songs capture pure nostalgia as well as this one.

“Emmylou” – First Aid Kit (2012)

“The bitter winds are coming in and I’m already missing the summer”

Johanna and Klara wrote this as a tribute to Emmylou Harris and Gram Parsons, who were big musical influences on the band. The song also references the rocky relationships that stars like June Carter and Johnny Cash endured, and how things ended up working out after all. It’s a hopeful piece that blends elements of the natural world in colder months with allusions to new beginnings.

“Stubborn Love” – The Lumineers (2012)

“When it got cold, (ooh) we bundled up”

No fall playlist is complete without a Lumineers song. I like this one because it fearlessly describes the joy in loving someone wholly despite their flaws. The dramatic tempo changes and an emotional buildup is introduced, making it a staple piece for any relationships being born or strengthened this season.

“Shine a Different Way” – Patty Griffin (2015)

“I’m gonna let it be the moon, let it play the tune, the one that keeps repeating”

This is the best song on the list in my opinion. It poetically encapsulates Griffin’s journey toward learning to accept life just the way it comes. Through metaphors involving sunshine, outstretched arms, and fields forgotten by the rain, she describes a euphoric realization that she is not in control of many of life’s complexities. I think that’s a mindset we can all adopt as autumn rolls around. 

“San Luis” – Gregory Alan Isakov (2018)

“I’m a ghost of you, you’re a ghost of me”

This is a classic example of right-person-wrong-time. Isakov moves the listener through highways, avenues and smoky hazes, trying and failing to identify a past love in everything he sees. The combination of his distant voice and folk-y guitar riffs give the song a wistful feel. 

“Whatever You Do” – Brandi Carlile (2018)

“There are days when I change with the weather”

Carlile survived a rocky past and isn’t afraid to be vulnerable about it in her songs. This one particularly touches on her willingness to accept all that has been thrown at her, to embrace all that is to come, and to courageously dissolve an attachment to someone close to her. This introspective piece feels like a breath of crisp, fresh air and a weight off your shoulders.

“Halloween” – Phoebe Bridgers (2020)

“Baby it’s Halloween, we can be anything”

In this song, Bridgers likens Halloween to the act of playing “dress up” as lovers when both people know the relationship has expired. Two skeletons slow-dancing is the best visual I can think of to represent it. Though the story is dark, it is also lyrically stunning, and I couldn’t go without paying homage to the holiday. 

“Twin Soul” – Christian Lee Hutson (2020)

“Our cheeks were frozen, watching the storm roll in”

Hutson’s debut album Beginners feels like autumn all around, but this particular track especially captures the season’s essence via hazy memories of cold weather and a first love. The melancholy end to a treasured relationship that Hutson sings about is both heartbreaking and heartwarming.  

“Two Haunted Houses” – Charlie Hickey (2021)

“I’ll walk through you if you walk through me, two haunted houses on the same street”

I love this song because of the obvious Halloween reference, but also because Hickey celebrates the eerie yet gratifying feeling associated with meeting someone as vulnerable and introspective as him. The piece is decorated with vivid memories of wandering Turnerman Road, letting a cat out of the house and wondering if this era of his life is too good to be true. 

Sydney Coleman

CU Boulder '25

Sydney is studying journalism and economics at CU. She moved to CO from MI in 2010, and during her time here she's enjoyed hiking, learning guitar, and practicing photography.
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