Photography by Harper Smith
From a small town in Iowa, Hailey came to Nashville to fulfill her childhood dreams in the music industry. She has collaborated with an array of talent, including Little Big Town, Trisha Yearwood, Brandi Carlile, Alicia Keys and many more. Her career took off in 2020 with her self-funded debut album The Dream and she has received CMT Music Award and Grammy nominations. Her song “Everything She Ain’t,” went viral on TikTok over the past year and has brought even more recognition to the rising star.
Hailey will be taking the main stage at Pilgrimage Music & Cultural Festival, on September 23rd at the Park at Harlinsdale Farm. We recently had a chance to sit down with her to learn a little bit more about her career and what lies ahead.
ARH: When and how did your music career begin?
HW: I was writing songs as a young girl and came to Nashville on vacation with my family when I was fifteen. We went to the Opry, and I immediately decided that I would chase my dreams and play on that stage one day. When I graduated from high school, I packed my bags and moved to Nashville to get my songwriting career started.
ARH: What artists influenced your style?
HW: Dolly Parton and Keith Whitley are some of my biggest influences. I also love the 90s country artists I grew up listening to – Alan Jackson, Patti Loveless, Trisha Yearwood, Deana Carter. Their songs were all so good.
ARH: Do you write all your own music?
HW: I write many of my songs but not all of them. There are so many incredible songs that are waiting to be heard. Whenever I’m putting an album together, it’s always “best song wins” whether I wrote it or not.
ARH: What has been the most challenging part of your career?
HW: Right before I cut my record The Dream, I was a waitress at a mom-and-pop Cajun restaurant; feeling deflated and wondering if music would ever work out for me. I decided to give it one more go before I decided to pack it up and head back to Iowa. I cut The Dream and released it independently. When other artists started to post about my song “Ten Year Town”. everything changed.
ARH: What goals do you have for the future?
HW: I’m hoping to buy a farm (with lots of piglets), in Iowa one day. That keeps me going- haha!
ARH: Did you anticipate that “Everything She Ain’t” would go viral? What inspired this song?
HW: I had no idea that a TikTok trend would get started with the song, but I have to thank the blue-collar boys of TikTok for making it happen! When I sat down with Bryan Simpson and Ryan Tyndell to write that day, we started with a dark ballad and kept getting stuck. I suggested we lighten the mood and try a different direction, and we started writing “Everything She Ain’t”. It came together so quickly; we were just on a roll.
ARH: How did you become involved with the Pilgrimage Music & Cultural Festival? What can fans expect from your performance?
HW: I cannot wait to perform at Pilgrimage! I have played it once before in 2021 and had a blast. This year I believe I’m playing the main stage, which I’m so excited for! My shows are full of fiddle and straight-up country music so I hope everyone likes it.
ARH: What do you love about Williamson County (home to the Pilgrimage)?
HW: I love the Franklin Farmers Market, and to hike around the Harpeth. It’s such a beautiful area of Tennessee!
ARH: If you could give advice to aspiring musicians what would it be?
HW: I always tell young artists that they should stay true to who they are and what makes them unique. It can be tempting to chase what’s popular in the music industry, but it’s best when you tap into your true self and share your art with the world.
See Hailey Whitters perform at Pilgrimage this month! Learn more and get your tickets at pilgrimagefestival.com. You can also see Hailey’s other tour dates at haileywhitters.com.