Caroline Milby is an indie art-pop singer-songwriter, producer, and former full-time attorney who is bringing her immersive project with avant-garde elements, Caroline in the Garden, to Cherry Street Tavern this Thursday, April 2nd, marking her debut in Chattanooga at the hometown favorite venue.
Caroline recently transitioned from practicing as an attorney full-time to embracing a career full-time in music, and she writes about the transformation, what drew her to it, and defying societal expectations with her debut album, Act Two, set to release on April 10th, 2026; however, there is early access to the album on Caroline’s Bandcamp page, a great resource for artists. Be sure to check out and support the album on Bandcamp.
The album is heavily piano-driven and carries with it introspective and emotional themes, with an emphasis on lyrics and a heavy exploration of the fear and freedom Caroline felt in making such a huge career and life change. It immediately reminded me of Kate Bush, especially on tracks like “Push Through,” which captures the essence of what she is trying to say on this album, with lyrics like “push through the doubt, make it about the transformation, make it about the restoration,” while showing her incredible versatility on the piano.
In speaking with Caroline about what fans can expect from her indie art-pop show at Cherry Street Tavern, she mentioned that there is an energetic exchange at the shows, with her often engaging the audience and hopefully empowering them.
“I like to have an energetic exchange at a show. I want to talk to the audience, share stories with them, go back and forth, and give them a vibe boost. Most of my songs are about confidence and empowerment, and I wrote them to inspire that in myself, as well as to give it to other people.”
When discussing her debut studio album and the journey to what she calls “unhinged art-pop,” Milby suggested that the album is a reference to the first act of her life, how society's expectations shaped her, and how she finally found the courage to break free and create her unique soundscape.
“Act Two is a reference to how I spent much of my early life, my Act One: following societies’ expectations of me. I was always active in music, theater, and performance but pursued a very practical path as an attorney, never really allowing myself to be “an artist” as anything more than a hobby.
By 2022, I was fed up with it, and I finally summoned the courage to start sharing my own music in wider circles and embracing myself as a creative force. The songs that I wrote during this time, about empowerment, authenticity, and the perils of only playing by others’ rules, are the ones that ended up on this album. I named it Act Two as a nod to how I had changed and how my path had changed as well.”
Caroline’s project is an example of what happens when you put your mind to something and follow your heart and passions in life, instead of letting society dictate them. I think her music is both groundbreaking and familiar at the same time, and that is a rare combo these days. Her vocals are warm, her lyrics expressive, and her message is incredible.
When asking Caroline about how excited she is to come to Chattanooga to make her debut at Cherry Street Tavern, she mentioned being based out of Atlanta and that she has visited quite frequently with her family and can’t wait to share her art-pop project with others.
“I’m from Atlanta, so I have visited quite a bit. My son loves the aquarium because he loves freshwater fish, so we were there really recently. My stepmother is also from Chattanooga, so I grew up visiting for family gatherings and reunions on her side.
I am excited for the nostalgia that it gives me to play in Chattanooga. Overall, I feel strongly about empowering people through song, so I want my audience to leave feeling great about themselves and their gifts in the world, and there may be a little souvenir surprise midway through the set to help that feeling stick with them.”
Caroline in the Garden
- 8 p.m. April 2nd.
- Cherry Street Tavern, 719 Cherry Street. Chattanooga
- $10
- facebook.com/cherrystreettavernchattanooga