I made this playlist in November 2025, but hadn’t gotten around to posting it officially on the blog until now. I was a bit unhappy with how it flowed at first, and also because it was so deeply an autumn playlist that posting it in the spring and summer felt like sacrilege. Well now that it’s the best month of the year (October) it feels like the perfect time to let it breathe on the blog. A good autumn playlist after weeks of summer shredders.

I’d been wanting to make this playlist since 2023 when I stepped out on a rainy fall morning, listening to Bridget St. John’s Ask Me No Questions, and felt a deep, melancholy-driven euphoria wash over me. I wanted something that felt cozy, a little beaten down, a little restorative. Also on here is Karen Dalton, Silvana Estrada, Joan Shelley, North Americans, Devendra Banhart, Cat Power and more. I listened the other morning and thought to myself, “damn you have another banger on your hands.”

All that being said, right now I am reading Liz Pelly’s fantastic Mood Machine book, talking about how Spotify has aimed to create background music or “laid-back listening” and creating a “vibe.” With all these playlists I’m making, I realize I’m falling into this trap of thinking that playlists are “healing,” or as I wrote before, “restorative.” They are actually just collections of songs that sound alright bunched together. But by golly it’s still fun to make them, and I hope you enjoy listening to them, too.

Listen To From My Windowsill on Tidal | Qobuz | Apple | Spotify

1. Karen Dalton – “Little Bit Of Rain”
2. Bridget St. John – “Autumn Lullaby”
3. Alela Diane – “Lady Divine”
4. Yo La Tengo – “Today Is The Day”
5. Bedouine – “Dusty Eyes”
6. Marina Allen – “Halfway Home”
7. Judee Sill – “Lopin’ Along Thru the Cosmos”
8. Silvana Estrada – “Como Un Pájaro”
9. Jessica Pratt – “Hollywood”
10. Linda Perhacs – “Sandy Toes”
11. José González – “Stories We Build, Stories We Tell”
12. Adrianne Lenker & Buck Meek – “Indiana”
13. Feist – “Hiding Out In The Open”
14. Joan Shelley – “Lure and Line”
15. North Americans – “Run Down”
16. Mazzy Star – “Give You My Lovin”
17. The Velvet Underground – “Pale Blue Eyes”
18. Mr Twin Sister – “I Want A House”
19. Emahoy Tsegue Mariam Gebru – “Homesickness”
20. Loving – “Blue”
21. Nick Drake – “Which Will”
22. Emily Hines – “Cowgirl Suit”
23. Cat Power – “Naked, If I Want To”
24. Devendra Banhart – “Will I See You Tonight? (feat. Vashti Bunyan)”
25. Jonny Nash – “Walk The Eighth Path”