18 Chilly Songs about October

October is a month that is often associated with the change of seasons, as the weather turns colder and the leaves begin to change color. It’s a time of transition, as the warm summer months give way to the colder, darker days of autumn.

This mood is perfectly captured in these 18 chilly songs about October. Each song has its own unique sound and style, but they all share a common thread of introspection and melancholy. From the hauntingly beautiful “October” by U2 to the soulful “October Song” by Amy Winehouse, these songs capture the essence of this transitional time of year.

They explore themes of love and loss, change and growth, and the beauty of the natural world. Some songs have a dreamy, atmospheric sound, while others are edgier and darker. Together, they create a musical portrait of October, a time of introspection and transition, where the past and future converge in the present moment.

1. October Song – Amy Winehouse

“October Song” is a hauntingly beautiful track from the late British singer Amy Winehouse’s debut album, “Frank.” The song showcases Winehouse’s soulful voice as she sings about lost love and heartbreak. The lyrics are emotive and introspective, with Winehouse’s poignant words painting a picture of a love that has faded away. The melody is simple yet powerful, with acoustic guitar chords and gentle percussion providing a mellow backdrop for Winehouse’s vocals. The song’s melancholic atmosphere is heightened by Winehouse’s raw, emotional delivery, making it a standout track on an already impressive album. Overall, “October Song” is a poignant, soulful ballad that showcases Amy Winehouse’s immense talent as a singer and songwriter.

2. October – U2

“October” by U2 is a reflective and atmospheric track from their second studio album, “October.” The song starts with a haunting piano melody and gradually builds up with the addition of drums, bass, and guitar. Bono’s vocals are soft and introspective, as he sings about the changing seasons and the passage of time. The lyrics are poetic and contemplative, exploring themes of loss, regret, and redemption. The song’s haunting melody and introspective lyrics create a sense of wistfulness and nostalgia, making it a standout track on the album.

3. October Road – James Taylor

“October Road” by James Taylor is a mellow and contemplative track from his album of the same name. The song features Taylor’s signature fingerpicking style on the acoustic guitar, as well as gentle harmonies and light percussion. The lyrics are introspective and personal, as Taylor sings about returning to his hometown and reflecting on his past. The song’s gentle melody and Taylor’s soulful vocals create a sense of warmth and nostalgia, evoking memories of childhood and simpler times. Overall, “October Road” is a beautiful and introspective track that showcases James Taylor’s talent as a songwriter and musician.

4. October Song – The Incredible String Band

“October Song” by The Incredible String Band is a psychedelic folk track that showcases the band’s unique sound and experimental approach to music. The song features intricate acoustic guitar work and unusual instrumentation, including sitar and dulcimer. The lyrics are surreal and poetic, describing a dreamlike journey through a mystical landscape. The song’s trippy sound and esoteric lyrics capture the psychedelic spirit of the 1960s, making it a standout track on the album. Overall, “October Song” is a captivating and unconventional track that showcases The Incredible String Band’s experimental approach to folk music.

5. October – Alessia Cara

“October” by Alessia Cara is a poignant and introspective track from her debut studio album, “Know-It-All.” The song features a simple yet emotive melody with acoustic guitar chords and minimal percussion, allowing Alessia’s soulful vocals to take center stage. The lyrics are personal and reflective, exploring themes of self-discovery and acceptance. The song’s emotive sound and introspective lyrics create a sense of vulnerability and authenticity, making it a standout track on the album.

6. Cold October – Escondido

“Cold October” by Escondido is a haunting and atmospheric track from their album “Walking with a Stranger.” The song features eerie guitar riffs and atmospheric keyboards, creating a moody and introspective vibe. The lyrics are emotive and introspective, exploring themes of heartbreak and loss. The song’s haunting sound and introspective lyrics create a sense of melancholy and yearning, making it a standout track on the album. Overall, “Cold October” is a captivating and introspective track that showcases Escondido’s talent for creating haunting and atmospheric music.

7. October – Broken Bells

“October” by Broken Bells is a dreamy and atmospheric track from their self-titled debut album. The song features ethereal synths, atmospheric guitars, and a driving beat that creates a mesmerizing sound. The lyrics are introspective and personal, exploring themes of nostalgia and the passage of time. The song’s dreamy sound and introspective lyrics create a sense of introspection and contemplation, making it a standout track on the album.

8. October Twelfth – Roy Harper

“October Twelfth” by Roy Harper is a melancholic and introspective track from his album “Stormcock.” The song features acoustic guitar work and Harper’s soulful vocals, creating a moody and reflective sound. The lyrics are poetic and introspective, exploring themes of love, loss, and regret. The song’s melancholic sound and introspective lyrics create a sense of longing and sadness, making it a standout track on the album. Overall, “October Twelfth” is a powerful and introspective track that showcases Roy Harper’s talent as a songwriter and musician.

9. October Nights – Yellowcard

“October Nights” by Yellowcard is a catchy and upbeat track from their album “Southern Air.” The song features driving guitar riffs and a pop-punk sound that creates an energetic and infectious vibe. The lyrics are personal and reflective, exploring themes of love and longing. The song’s upbeat sound and introspective lyrics create a sense of optimism and hope, making it a standout track on the album.

10. Before October’s Gone – Cimorelli

“Before October’s Gone” by Cimorelli is a gentle and introspective track from their album “Sad Girls Club.” The song features gentle acoustic guitar chords and Cimorelli’s soulful vocals, creating a moody and emotive sound. The lyrics are personal and introspective, exploring themes of change and letting go. The song’s gentle sound and introspective lyrics create a sense of melancholy and reflection, making it a standout track on the album. Overall, “Before October’s Gone” is a touching and introspective track that showcases Cimorelli’s talent as songwriters and musicians.

11. October Trees – Ron Pope

“October Trees” by Ron Pope is a haunting and introspective track from his album “Calling Off the Dogs.” The song features acoustic guitar work and Pope’s soulful vocals, creating a moody and introspective sound. The lyrics are personal and reflective, exploring themes of nostalgia and the passage of time. The song’s haunting sound and introspective lyrics create a sense of melancholy and yearning, making it a standout track on the album.

12. October – Jonas Alaska

“October Trees” by Ron Pope is a haunting and introspective track from his album “Calling Off the Dogs.” The song features acoustic guitar work and Pope’s soulful vocals, creating a moody and introspective sound. The lyrics are personal and reflective, exploring themes of nostalgia and the passage of time. The song’s haunting sound and introspective lyrics create a sense of melancholy and yearning, making it a standout track on the album.

13. Last October – Kidd G

“Last October” by Kidd G is a melancholic and introspective track from his EP “Teenage Dream Part 1.” The song features a simple beat and Kidd G’s soulful vocals, creating a moody and emotive sound. The lyrics are personal and introspective, exploring themes of heartbreak and loss. The song’s melancholic sound and introspective lyrics create a sense of sadness and reflection, making it a standout track on the EP.

14. October Grey – The Screaming Jets

“October Grey” by The Screaming Jets is a brooding and atmospheric track from their album “Chrome.” The song features a heavy guitar riff and a driving beat that creates a moody and intense sound. The lyrics are introspective and personal, exploring themes of pain and regret. The song’s brooding sound and introspective lyrics create a sense of introspection and darkness, making it a standout track on the album. Overall, “October Grey” is a powerful and introspective track that showcases The Screaming Jets’ talent as a rock band.

15. October Snow – Jeremy Zucker

“October Snow” by Jeremy Zucker is a dreamy and atmospheric track from his album “Brent II.” The song features Zucker’s delicate vocals and electronic beats, creating a moody and contemplative sound. The lyrics are personal and introspective, exploring themes of love and loss. The song’s dreamy sound and introspective lyrics create a sense of melancholy and reflection, making it a standout track on the album.

16. We Fell in Love in October – Girl in Red

“We Fell in Love in October” by Girl in Red is a sweet and charming track from her album “Beginnings.” The song features acoustic guitar chords and Girl in Red’s tender vocals, creating a mellow and romantic sound. The lyrics are personal and intimate, exploring the ups and downs of a new relationship. The song’s charming sound and intimate lyrics create a sense of warmth and nostalgia, making it a standout track on the album. Overall, “We Fell in Love in October” is a beautiful and romantic track that showcases Girl in Red’s talent as a songwriter and musician.

17. One October Song – Nico Stai

“One October Song” by Nico Stai is a haunting and introspective track from his album “Park Los Angeles.” The song features Stai’s soulful vocals and a simple acoustic guitar, creating a moody and emotive sound. The lyrics are personal and introspective, exploring themes of regret and nostalgia. The song’s haunting sound and introspective lyrics create a sense of melancholy and reflection, making it a standout track on the album.

18. October Sun – Matt Berry

“October Sun” by Matt Berry is a whimsical and charming track from his album “Witchazel.” The song features a catchy piano melody and Berry’s distinctive vocals, creating a playful and upbeat sound. The lyrics are witty and playful, exploring themes of love and the changing of seasons. The song’s whimsical sound and playful lyrics create a sense of joy and lightheartedness, making it a standout track on the album. Overall, “October Sun” is a delightful and charming track that showcases Berry’s talent as a musician and songwriter.