Cover Story
Gayle Skidmore: Hummingbird in a Whirlwind

Gayle Skidmore. Photo by Anastasya Korol.
Gayle Skidmore is a whirlwind. Tall and blonde, like some kind of Norse goddess who ditched the mountaintop for a folk club, she walks into a room and immediately rewrites the energy. She’s gentle, glowing, generous. She is also wildly prolific, unnervingly smart, and intimidatingly good at everything. She plays more than 20 instruments, has written over 2,500 songs, and somehow still finds time to illustrate coloring books and drop Finnish-language EPs for her family in Lapland.
She’s a hummingbird with a piano strapped to its back.
That’s the only way I know how to describe her. Fast moving. Joyful. Built for flight but carrying weight most people wouldn’t dare touch. She makes art because she has to. Because it pours out of her. Because it’s how she breathes.
We’ve been in each other’s orbit since 2015 or thereabouts, part of the same San Diego music scene. I’d seen her perform at Lestat’s Open Mic, and the impact was lasting. But over the last two years, since she returned from living abroad, Gayle has become something more to me. A friend. As a career musician myself, inspired by women like Joni Mitchell, who never took the easy route, I can tell you without hesitation that Gayle is the real deal in the same category. She’s the kind of artist I once only dreamed of calling a peer. A whimsical goddess for whom the wind brings inspirations for song and laughter. She means it when she shows up, and she always shows up as her whole self.
And that’s what this story is about. The whole self of Gayle Skidmore. The magic, the trauma, the talent, the tenderness. The whirlwind.
“Songwriting isn’t so much what I do as who I am,” she told me. “Whether or not I am focusing on writing, I hear songs in my head. While sometimes it is voluntary, quite often I’ll simply notice that I am humming something, and I’ll stop to write it down or record a voice note. So, I keep creating because that is how I live my life.”
It shows.

Gayle’s roots go back to childhood tape decks and teasing siblings. “My sisters only hit record for me and then teased me for years about my little songs,” she says. “I wouldn’t say it was collaborative, sadly, but I did have the desire to record my songs early on.” By middle school, she’d formed a duo with her friend Kathleen. “My dad had a mic that could record to a tape deck, and we recorded enough of our little collaborations to fill up a tape. I still have one, but our friend rewound it with a crayon instead of a pencil, and I’m pretty sure that ruined it. ’80s/’90s kids will understand.”
Her early performances were classical piano recitals. “I was extremely afraid of performing and terrified of making mistakes,” she says. “I’ve had to unlearn a lot of that,” which is wild to think about now because on stage, Gayle is magnetic. Her music might be emotional, even devastating at times, but in person, she’s disarmingly funny. It’s that balance that makes her impossible to look away from.
“A lot of my songs can be very serious and melancholy, but my personality on stage leans more into my quirky sense of humor,” she says. “My songs often bring people to tears, but I also really love making people laugh and sharing moments on stage that feel like inside jokes with the audience.”
Germany’s Süddeutsche Zeitung once called her Die Schutzpatronin der Gartenzwerge: The Patron Saint of Garden Gnomes. “This title always reminds me of the film Amélie, one of my favorites, which I feel combines sincerity, humor, and melancholy in an exquisite fashion,” she says. That checks out. Gayle is Amélie with a dulcimer and a trauma history.

And yes, trauma plays a role in her songwriting. She doesn’t hide that. About 14 years ago, her boyfriend at the time had a mental health crisis that left her shaken. “I was unprepared to deal with it and ended up suffering with PTSD because of the traumatic way it played out,” she told me. “A few days after he landed in a psychiatric hospital, I left to go on a three-month tour from San Diego to New York and back by myself. Writing songs through that time kept me alive. I did not have many friends who were able to walk through that experience with me, and songwriting became my best friend, confidant, and safe place.”
One night, on the side of the road just outside Albuquerque, a song called “Little Bird” came to her. “At the time, I didn’t know how to pray anymore. I was shaken to my core and in incredible pain, as my boyfriend and I had planned to get married. This song became my way to pray and ask for comfort. It’s often my way to pray for others.”
If you’re thinking this sounds like therapy, you’re right. But it’s more than that. “I’ve known I wanted to be a singer from the age of eight, when I told my parents that,” Gayle says. “Other moments of realization have come to me over the years, and when I’ve felt discouraged in the music industry, looking back to those moments has kept me going.”
Gayle recently released a 3-song EP iin Finnish. So beautiful!
One such moment came in 2007, when she met speaker and author Nick Vujicic. “That is a really long and deeply personal story for another time,” she says, and I can tell it’s sacred. So, we leave it there.
Gayle’s creative palette is wild and extensive. She’s classically trained on piano, sure, but she also plays dulcimer, balalaika, banjo, harp, and anything else she can get her hands on. She sees herself as a singer-songwriter, “mainly,” she says. “I’m mostly just a pianist, and the rest I play for fun.”
As modest as that sounds it doesn’t hold water. Her instrument choices are intentional, emotional. “The tone and personality of the instrument deeply affects the mood and expression of each song, so I try to choose the instrument based on what I want to convey,” she says.
That’s the thing. Everything she creates is about meaning. She weaves sound, story, and image into one whole expression. She once released an album with a coloring book. Not because it was trendy (this was 2009), but because it made sense to her.
“When I first released my coloring book in 2009, it was not a trendy thing. I like to say that I started the adult coloring book trend, and I was in rooms with influential people who perhaps could have taken my idea and run with it. Ha ha. Sitting down and listening to an entire album used to be a sacred ritual for so many of us. When I did that, I’d often draw or paint, and found it very cathartic.”

She was awarded the Kassan Foundation Grant for that coloring book, which accompanied her album The Golden West. And she’s only grown from there. “Since then, I’ve devoted a lot more time to the art that accompanies my releases and love what I came up with for my most recent album, The Ashtabula River Railroad Disaster. This album comes with some digital art I drew in Procreate over many, many hours.”
Music is visual for her. “I have a musical world in my head, and I like to create space for other people to join me there,” she says. “It is full of whimsy because that fills my heart with joy. I am mostly drawn to films, music, and people who are full of flights of fancy. It makes life bearable to be filled with wonder when our hearts will permit us.”
That album, Ashtabula, is based on a real 1876 railroad disaster that killed one of her distant relatives, the hymn writer Philip P. Bliss. “I had to know more,” she says. “The more I learned, the more I was gripped by this tragedy. I was moved to tears by several of the articles I read, which were written directly after the event, and felt I needed to express what I was feeling.
“I wrote a bit about each of the pieces in my sheet music, story and art book that accompanies my album. I’ve always wanted to release a solo piano album, and hope this will be the doorway for me to compose many more albums in this genre.”
Gayle Skidmore didn’t just return to San Diego after eight years abroad with souvenirs and cute stories to share. She came back with sharper instincts, a deeper well of sound, and the kind of artistic grit you only get from starting over in a country where no one knows you play 20 instruments and write songs in your sleep. “I definitely grew in my recording skills over there,” she says. “I absolutely loved collaborating with Maya Fridman from the label TRPTK, and she inspired me so much with her utter commitment to her art and skills.” It wasn’t always easy, but it cracked something open. “My outlook has sharpened because of the experience of being out of my element and having to start over abroad made me value the community of San Diego even more.”

Gayle with her cousins in Kittila, Finland, wearing traditional clothes.
And we value her right back. Having someone of Gayle’s caliber in our backyard again feels like winning the local lottery. She’s a Grammy-level songwriter playing hometown venues, weaving sonic spells right here where we live. San Diego doesn’t just claim her—we celebrate her.
“Being on my own quite a bit made me dive into my back catalog of music and think more about what direction I want to head in with my music. I feel like I finally really reached that with my single ‘All My Life,’ which I recorded with Jeff Berkley.”
And still, she pushes herself to try new things. When her electro swing song “Viva La Vita,” co-written with Brandon O’Connell, was playlisted by Berlin’s Electro Swing Thing label, it opened a door. “I collaborated on a song called ‘Dance Alone’ with Dutch producer LVDS,” she says. “I enjoyed working on this track so much because although I’ve worked in other genres while writing for TV/Film, this was one of the few I’ve done in a completely different direction under my own name. It’s my most streamed song on Spotify, currently, so that’s also exciting.”
Despite her extensive acclaim, including winning multiple San Diego Music Awards, she stays grounded. “I really appreciate when there is a positive response to what I’m doing, but it has never really interfered with what I do creatively,” she says. “Life is short and precious. I’m very grateful to have the affirmation of the SDMAs and other awards, but at the end of the day what I’m really trying to achieve is to create music and art that I love and am proud to leave behind when I’m gone.”
A cut from Gayle’s new album (reviewed this month: https://sandiegotroubadour.com/?p=29885)
“The most important accolades I have ever received are the grateful tears of folks at my shows who have left feeling less alone or feeling understood for a moment. That is a privilege to me and is something I work for. I want to be sincere in my art—whatever the genre, whatever topic I’m writing about.”
So how does she do it all?
“I drink a lot of coffee,” she says. “I’ve got a LOT of irons in the fire right now, and I’m expecting to release several songs in various genres this year. I released an EP in Finnish for my family in Lapland, Finland, and hope to release a full-length this winter. I’m wrapping up the next electro swing tune, and I’m working hard on a list of 100 songs that I previously released on Patreon. I’ve categorized them by genre and am going to release them as albums as I’m able to finish them.”
Gayle Skidmore is always creating. Not to impress anyone. Not to win. But because she has to. Because it’s how she stays alive. And lucky for the rest of us, she keeps doing it.
She’s a hummingbird in a whirlwind. She’s got a piano strapped to her back. And she’s flying straight into the next song.