New York has a way of bringing out the strange, the intimate, and the unexpected in artists. For singer-songwriter Kara Arena, music lives somewhere in that space, between structure and spontaneity, vulnerability and experimentation. With her September 28 show at City Winery, just steps from Chelsea Market, coming up this week, we talked with Kara about the records that shaped her, making music in New York, and finding the beauty in the messiness of creating. PRESS PLAY.
★ Describe your music in three words:
Kara Arena: Of The Earth
★ What was the record that first made you think, “I want to make music!”? What was it about that album that hit you so hard?
Kara Arena: It was the music of Rickie Lee Jones that actually made me want to start writing. I had never heard music that defied the rules in that way before. Her blend of jazz, folk, pop, and spoken word create a genre of its own. She is not tied down to song structure, rhyme schemes, or anything else we associate with “how a song works”. When I heard her music, I thought, ‘maybe I could do my own version of this’. Her way of working inspired me to find the messiness in my own craft- a reflection of the way thoughts and feelings come through in real time. And the people who are into that sound will find their way to it.
★ New York has been home to so many great musicians and songwriters. What is it about the city that inspires so much great music?
Kara Arena: I think people often come to New York with a purpose. And when you have a purpose, you have something to say. Life in this city can be vibrant and wonderful, but it is not a comfortable place for an independent artist to make a living. So if you’re sticking it out here, it’s usually because you believe you have something to offer that nobody else can. And when those artists make it through, they’re carrying with them the seeds of all the dreams they started with…and all the fight it took to stay here. It’s easy to fall in love with that when you see it onstage or hear it in a song.
Her way of working inspired me to find the messiness in my own craft.
★ What’s the most unexpected or surreal music moment you’ve experienced in New York, the kind of night you still can’t believe actually happened?
Kara: I like to host pop up shows in unexpected places in the city and I try to create memorable experiences for the audience to take in the music. I recently produced a show in an empty storefront on Bowery on a rainy, spring evening. Traffic to the venue was crazy and I was running late as I headed to the space with a caravan of rugs, blankets, candles, lamps and equipment. Somehow in less than an hour, we transformed the space from an empty room to an intimate concert venue, sound checked, and started the set. Passers-by stood outside in the rain to check out the performance that was happening inside. I couldn’t believe we pulled off this last minute, thrown together gig and to this day it is my favorite show I’ve ever played.
★ If we threw three records into a blender to make the sound of Kara Arena, which three would you pick, and why?
Kara: I think if you like the vulnerability and introspection of Joni Mitchell’s “Song to a Seagull”, the mysticism and folklore of “alterum” by Julie Fowlis and the cinematic scope of Alela Diane’s “Cusp”, I think you might like my work.
★ You’re playing City Winery on September 28. What kind of night are you hoping to create for everyone coming out?
Kara: I’m embracing a more communal sound and I’ll be sharing the stage with some of my favorite musicians. They all help me keep the spontaneity alive in the room while preserving the intimacy that I think these songs naturally hold. I’ll also be joined by an old friend and gifted songwriter, Juliette Stewart, for our first collaboration since performing in musicals together as children. Worlds will be colliding on stage and I’m excited to have this show as a marker of how far we’ve come and where we’re all headed. ★
Kara Arena with Juliette Stewart
City Winery NYC
Monday, September 28, 2026
7:00 PM
More from Kara Arena here