Hailey Whitters has an endearing habit of suggesting she’s perennially late to the party. “I’ve always just felt like a late bloomer,” she says, with a sigh that turns into a laugh. She’s awfully hard on herself. Whitters grew up in Shueyville, Iowa, population just shy of 600. “It’s such a little town. It’s getting bigger, but we don’t even have a post office,” she says. “We have two bars, a wine cellar, and a church.” The oldest of six children born to a large Catholic family, Whitters grew up a determined but unexpected artist, drawn to songs and singers but unsure why. “I didn’t grow up in a super musical family,” she says. “I just had a weird inkling to do music.” The Dixie Chicks, Trisha Yearwood, Patty Loveless, and other women who drove 90s country radio were her gateway heroines, which led to a deep dive into classic country, and ultimately, Americana storytellers such as Patty Griffin, John Prine, and Gillian Welch. “I took my first trip to Nashville when I was 16 and fell in love,” Whitters says. “I immediately knew I wanted to move here.” A year later, she did. She also enrolled in college, and paid her proverbial dues as a nanny, waitress, and salon receptionist before signing with left-of-center lighthouse Carnival Music in 2012.