Hailey Whitters’ success over the past year is a testament to the hard work she’s put in for 15 years prior. She’s now celebrating the small moments that led to the big achievements, such as performing at 2023 Pilgrimage Festival. She made her Pilgrimage debut in 2021 performing on one of the side stages, and now two years later, Whitters is set to take the main stage on Saturday (September 23).
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Lately, she’s been enjoying the success of her breakthrough hit “Everything She Ain’t” which reached the Top 20 on country radio. The song helped earn her an ACM Award for New Female Artist of the Year in 2023 and a nomination for Best New Artist at the 2023 CMA Awards, among many other high points.
Below, the Iowan chats with American Songwriter about what makes Pilgrimage unique, the impact of winning her first ACM Award and explains what exactly a “corn skirt” is.
American Songwriter: How did the opportunity to return to Pilgrimage come about?
Hailey Whitters: I’m not entirely sure. But I’m very excited to do it on a big stage this year. We did it a few years back and we did a smaller stage. It was really cool. It feels so strange to be playing a Nashville show these days because we’re always out on the road in all these different places. It’s really nice to be able to play Nashville and get to see our fans here. It feels a little bit like a hometown show and [to] go home and sleep in your own bed at the end of the night, it’s pretty awesome.
AS: What was it like making your Pilgrimage debut in 2021?
HW: It was so fun. It was coming back off the pandemic for us, so I think that was the corn skirt era. I was wearing my corn skirt all the time, it was awesome…I have a denim skirt that has these really massive sequin corn cobs on it. Fables by Barrie is her Instagram handle. She makes all these incredible outfits for Dolly [Parton] and she reached out to me and said she wanted to make me something. She made me this really awesome corn skirt and I wore it pretty much our whole festival, touring season.
Pilgrimage is one of those festivals, it’s always such a great lineup and it’s always just as a music fan, one of those festivals that you dream about getting to play someday and sharing the bill with so many really cool and diverse artists. It was really cool, it was exciting, and I was really glad that we got to play. I don’t know if it’s because it’s Nashville, but for me, it just feels so chill. It really feels like you’re getting to see some of the best artists in your backyard. It’s got a really chill atmosphere and everyone’s out there having a good time. I also think they always get such a cool mix of artists out there.
AS: How did it feel to win ACM New Female Artist of the Year? What does that award mean to you?
HW: That was insane. I was so excited to be nominated. It was my first time in all the 15 years that I’ve been here to be nominated and it was such an honor. I remember the day I was supposed to find out, I didn’t hear anything. I was kinda bummed and I turned off my phone for the day, went out got a little reset in the backyard with my dog. Then the next morning I got a call from my manager and they were like, ‘You won.’
I was feeling a lot of emotions and it made me really emotional because I have been in this town for 15 years, and it hasn’t been a quick, easy trip. It’s been a lot of setbacks and rejection and being told no and wondering if it was ever going to happen. It really made me emotional and feel really grateful for the people around me and the people in this town who believed in me and who kept me going. It was a really sweet moment.
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AS: What are some of the challenges that you’ve had to overcome and what have you learned or gained from those challenges?
HW: I think the biggest thing I always think about is the mental toll that this business can take on you. It’s constantly being told to change who you are or be different. I remember being told, “We already have enough girls.” I think being in this town and really believing in something and being told by everyone else it’s not gonna work, that is not fun. But I think that there’s also people who do believe in what you do and I think that it’s important to focus on them and on the fans and no matter how small that little group may be at the time, really pour yourself into it. I do think that if you work hard, it will all turn around and eventually it’ll see the light of day.
AS: When did you start to feel things shift in your career?
HW: It’s been a lot of different times. It’s been interesting because my whole career hasn’t been one defining moment that changed everything. It’s been a series of small moments. I think that the first big one is when I dropped “Ten Year Town” and I was waiting tables at the time and I didn’t have any team around me or anything. I just posted the song on my Instagram and Maren Morris heard it and reposted it, invited me to come out on her Girl: The World Tour. I remember that reignited the town around me.
I think the next big moment was signing my record deal. I signed my record deal in the middle of the pandemic and that was really crazy, but that was one of those moments that got me going again. It’s been a series of small breaks. Even from “Ten Year Town,” it hasn’t been one moment that changed everything.
AS: What can we expect from your set at Pilgrimage and how is it going to look or feel different than when you were there in 2021?
HW: We got a fiddle in the band. It’s country music, man. It’s high energy, it’s fun. I think people can expect to have a good time. It’s just a good time over here. We keep it light, we keep it fun. It is a Nashville show, so maybe we’ll have to pull out some more of the deep cuts and see how that goes over.
Photo Credit: Harper Smith/Courtesy Big Loud
