October is one of my favorite months, containing my favorite holiday of the year. And while many people think of ghouls, goblins, and ghosts when you bring up this month, the real themes that are associated with it are much more beautiful. Falling and changing leaves, the dying of the world as winter creeps in, and cool weather are just part of what makes this time so special.
In this article, we’ll dive into the 25 best songs about October and include a few surprise tracks that play on the month’s main themes.
1. October Song – Amy Winehouse
Amy Winehouse’s October Song doesn’t actually talk about the month, so it is an odd one to start our list off with. The track is actually about being a bird and flying away from everything to paradise. This one came from her debut album, and it was a great way to showcase her vocal talents in rhythmic soul songs.
2. October – U2
U2 sure does love to experiment with their sounds, but their single October takes it a step further. Nearly an instrumental, it spends its two short verses critiquing the materialistic nature of society and focuses on spiritual themes in the process.
The song destroys consumerism and uses fall and October specifically as a metaphor for the decline of life as the season changes from spring and summer abundance. Political and social commentary can be a hard thing to nail, even for a band as good at it as them, but this one does a great job of it.
3. October – Alessia Cara
October by Alessia Cara is the perfect road trip song. It’s full of wonder and has an adventurous spirit about it, very indicative of the inspiration for the track. She wrote this song based on her experiences going on tour with another singer and being excited and happy about the experience. It ends a bit on the melancholy side though, as she reflects that she will be sad when it’s all over.
4. we fell in love in october – Girl In Red
Some October songs are scary, discussing eerie and haunted places and ghoulish monsters. Others, like Girl In Red’s we fell in love in october are much happier. They wrote this track that likens the falling of leaves in October to her falling in love with her girlfriend in that month. It’s a beautiful and happy song to warm you up a bit as the cool autumn breezes move in.
5. October Sun – Matt Berry
October tends to be a time of change in weather patterns, with cool and warm air mixing to create swirling storms and rapidly-changing patterns above us. The ominous feeling that comes with watching a dark bank of clouds roll in is the one evoked in October Sun by Matt Berry. He compares the black clouds to a repeating bad dream that haunts him and discusses painful experiences in the singer’s past.
6. October – Evanescence
October by Evanescence is a song that’s shrouded in mystery. The track never mentions the month of October and frankly doesn’t seem to make a whole lot of sense. There are several different ways to look at the meaning of the song, but most of them boil down to the protagonist being too sick of things the way they are to stay in her current situation, but struggling with leaving because she’s tired of running.
7. October Nights – Yellowcard
October Nights is perhaps the best love song Yellowcard ever produced. Harking back to October nights laying next to their lover, the protagonist of the track details how much they loved sleeping side-by-side with their lover and how he could just gaze at her as she slept. It’s a beautifully poetic song, and one full of hope. No matter what happens down the line, he hopes that the two make it work together.
8. When October Goes – Barry Manilow
When October Goes‘ lyrics were originally written by Johnny Mercer, but it was never finished. Barry Manilow came along and matched it with a melody, transforming the incomplete work into a ballad. The two worked closely together up until Mercer’s early death at the hands of brain cancer, and Manilow worked wonders with the lyrics. He produced a hit song that peaked at number six on the Adult Contemporary charts in the US.
9. October Road – James Taylor
October Road was the title track of James Taylor’s 2002 album and was all about him heading back home. It served as a nostalgic traveling song that used the metaphor of the autumn season, embodied by the month of October. Just as leaves fall from trees in the fall, the singer is dealing with hardships and losses, metaphorical leaves falling in his life that must be dealt with, and going home offers some measure of support.
10. October – The Helio Sequence
The Helio Sequence’s October deals with the problems that come along with relationships. Everyone is going to mess up a good relationship at some point and make mistakes that hurt the people we care about. The important thing to remember is that you can learn from those mistakes and you don’t have to repeat them. Rather than regret them and let them affect future relationships, build from them and do better the next time.
11. October Trees – Ron Pope
From learning to relationships to watching one end, October Trees by Ron Pope discusses a cooling relationship that is almost over. Playing on autumnal themes of loss, the song is reflective regarding the troubled relationship the singer is in and frustrated that he feels as though he isn’t enough for his lover.
12. Leaving October – Sons of the Desert
Sons Of The Desert released Leaving October in 1998 and saw it do fairly well on the US Country charts. The song is a ballad about a narrator missing his wife who had died in the month of October, coming off as an extremely powerful and emotional homage to the fictional woman in the track. The narrator does realize that living in the past will take away his future and he is looking forward to eventually leaving behind the painful memories of her loss.
13. October Skies – Mumford and Sons
October weather is something to behold for the Northern Hemisphere, and Mumford And Sons collaborated with National Geographic to find striking October weather visuals for this song. October Skies plays on the colorful sunrises and sunsets that come out during the month, imagining the narrator looking up at those skies and seeing someone they care for. It was a bit out of the band’s typical sound, but nonetheless, an astounding piece of work.
14. My October Symphony – Pet Shop Boys
Red October is the common way to refer to the Russian Revolution that happened in the month of October—there were a lot of revolutions but only one contained in the month. My October Symphony takes a look at the politics that follow revolutionary events, reminding listeners that it’s the victors who write the history books and that heroes are often made in that writing.
15. October Rust – Tears of Magdalena
Tears Of Magdalena is a small Finnish group that combines orchestral arrangements and heavy metal—a beautiful and interesting combination. Their song October Rust is all about the leaves changing color in the autumn, with the dying color of the leaves being reminiscent of rust. As a whole, the track is a reflection on individual mortality, as just like the leaves, we will one day fade and fall.
16. Last October – Superheaven
If you’re an old fan of grunge bands like Nirvana but want to find someone new to look into, you should check out Superheaven. Last October is another one of their alternative songs that plays up the narrator spending the month of October—last year—crying and feeling helpless. It’s a track cut from the same cloth as the old depressing grunge music but has more of the hard rock sound that you might expect.
17. Waiting for October – Polaris
Perhaps nobody played on the impending end of the year that begins with October better than Polaris. Waiting On October seems to be about the singer waiting for an apocalypse to happen, referencing several ‘world-ending scenarios’ like Y2K in 1999. Ironically, the song was made for the Nickelodeon show The Adventures Of Pete And Pete, so it’s likely one that 90s kids are familiar with.
18. Eight Times Over Miss October – Clutch
Some of the most fun, yet eerie, songs out there are about getting cursed by a witchy woman. Clutch pulled off another great one with Eight Times Over Miss October. The titular Miss October is entirely fictional, but in the track, she curses the singer numerous times due to a perceived slight or bad experience with them.
19. Hymn to Red October – Basil Poledouris
Hymn To Red October plays on our previously mentioned Russian Revolution, but was composed for the film The Hunt For Red October, which saw Russia invading the US during the Cold War. Basil Poledouris scored the film, and this piece that references the 1917 revolution was used in the movie to build tension for the onscreen action.
20. This October – Julie London
Julie London’s Calendar Girl album featured a song for each of the 12 months of the year. An influential figure in the early film and jazz worlds, her 1956 release of This October was incredibly successful. The song mainly describes budding relationships in the cooling weather, an accurate depiction of the cuffing season 60 years ahead of the phrase being coined.
21. October Country – October Country
October Country is interesting because they recorded a singular, self-titled album in 1967. The title track is a fun psychedelic rock song that rambles about and doesn’t seem to make a whole lot of sense. From the gist of the lyrics, the band is remembering a particularly fond time they had in October, wanting to remain in that moment forever.
22. October Moon – Shahin & Sepehr
October Moon is a beautiful instrumental piece that’s driven by Spanish guitars. Shahin & Sepehr pull inspiration from a lot of genres, including flamenco, jazz, new age, and soft rock. Their creativity is on display in this short piece, perfectly encapsulating the essence of an October night without ever speaking a word.
23. Forest Of October – Opeth
Forest Of October is a standout song on this list because Opeth’s sound is purely heavy metal and death metal. The track itself describes a land in decline that’s nearly free of any life and gives off the narrator’s feelings of wanting to escape their hellscape. This one isn’t really for the faint of heart, as the song is very heavy and lasts for over 13 minutes.
24. One Night In October – Little Comets
One Night In October might come off as a happy song if you only listened to the upbeat instrumentals it comes with. But that, unfortunately, is far from the case. This one describes a relationship fraught with lies and arguments, using a particular night in October as the titular example of their toxicity.
25. Wake Me Up When September Ends – Green Day
Technically speaking, this song is about October. Because October comes after September, and the singer wants to be woken up after September ends, I’m counting it. Everyone knows Wake Me Up When September Ends by Green Day, but few know the real story behind it. Frontman Billie Joe Armstrong wrote the song after his father passed away from cancer, and it mainly depicts his sadness each year during the month when his father died.
As a contributing writer for Music Grotto, Dakotah writes and produces professional music/media content. He works closely with editorial staff to meet editorial standards and create
quality content for the Music Grotto website. Dakotah is passionate about music in a wide variety of genres, from hip-hop to country and lo-fi to metal, and he enjoys creating music pieces for Music Grotto.