Rising country star Hailey James is already leaving her mark on the industry—having received multiple awards from the Midwest Country Music Organization. Photos: Chris Emeott
The artist is a rising star in the country music scene.
One local singer is making a name for herself in the country music scene as a six-time award winner from the Midwest Country Music Organization (MCMO), receiving titles such as Female Vocalist and Songwriter of the Year, New Artist, Song of the Year and more. But before she was the singer and songwriter that she is now, Hailey James was a shy teenager in Cottage Grove, performing in school musicals with growing talent and a dream. “I kind of got into music when I was 10 or 11 years old,” she says, adding her love of choir and musicals started as a hobby and a passion. Now, it’s her full-time career.
Inspired by other country music artists, Hailey says eighth grade is when she picked up a guitar and taught herself how to play. Her father, AJ Trzebiatowski, recalls her earliest interest in becoming a professional musician. “Hailey and I used to watch America’s Got Talent … As we’re watching, she turns to me—and this is before I knew she wanted to do anything in music—and she said, ‘Dad, I want to be a country singer,’” he says. “For that Christmas, she asked for a Keith Urban guitar, a DVD and amp set, so she could learn how to play guitar.”
The TV show America’s Got Talent, which Hailey James and her father, AJ Trzebiatowski, watched together, inspired Hailey to pick up the guitar. She was only in eighth grade.
So, Hailey began writing music and took an interest in open mic nights. Her first gig was at the former Country Nights Saloon in Hastings. She was approached by the owner who wanted her to perform regularly.
At only 14 years old, Hailey took the stage every Thursday night for an entire summer. “At first, I only knew how to play maybe five songs. I had to learn more songs really fast,” she says with a laugh.
The opportunity was a turning point. While Hailey doesn’t recall details of the very first performance, she says those first few nights on stage were intimidating because she was shy and didn’t have any stage presence experience. Still, Hailey truly emerged as an artist that summer. Not only did she learn more songs, but she also became a performer. “It changed everything,” she says of the experience. “I became really comfortable on stage.”
A young Hailey James, 14, at one of her earliest performances—the former Country Nights Saloon in Hastings. Photo: Julie Trzebiatowski
Within a year of her Country Nights Saloon performances, Hailey recorded and released her first single, Live Your Life, a song about being true to yourself and not letting fear hold you back. The song brought attention to Hailey through radio plays, interviews and more performances. She also joined the MCMO, and now she had a community of artists cheering her on. Hailey’s mother and Woodbury resident, Julie Trzebiatowski, says the organization was “huge in shaping her musical path as the community is based on the philosophy of, ‘As one ship rises, we all rise.’” Of joining the MCMO, Hailey says, “They really uplifted me. People told me they thought I had something, and it really gave me confidence to take music even more seriously.”
That support helped Hailey realize music was in her future, but she says there were still challenges, most of which were internal. “The biggest struggle I had was self-doubt,” she admits. “I would wonder if I was actually good or if people really liked my music.” Hailey acknowledged that struggle is likely something many, if not all, artists deal with. However, she says navigating those feelings on top of just being a teenager wasn’t the easiest combination. “I went through some tough stuff, including being bullied,” she says. “But music was my safe space. I could go to my room, pick up my guitar and just write how I felt. It was like therapy for me.”
Cadott, Wisconsin’s, Hoofbeat festival includes three days of live music. In 2025, Hailey James opened the festival. That summer, on the evening of June 26 and in front of 20,000 fans, Hailey performed You Look Like You Love Me alongside headliner Riley Green. Photo: SamCrabtree
Through it all, she listened to the voices of people telling her she had a gift and chose to focus on the positives, including her biggest influence: Carrie Underwood. James says she recalls hearing Underwood’s song Blown Away on the radio and was mesmerized by her voice. AJ recalls a young Hailey listening and singing along to the same Underwood CD night after night. Knowing she wanted to find her own sound, Hailey says it took about six years to develop it. “My first few songs, I didn’t really have my own sound yet,” she says.
The Woodbury Days crowd was treated to a Hailey James performance on August 22, 2025. Photo: Julie Trzebiatowski
Hailey began performing at more restaurants, including Carmine’s in Woodbury, and events, such as Woodbury Days. In those early days, each performance was managed, marketed and set up by her parents; and with each one, she started discovering her own voice. As she recorded new music, Hailey says she was influenced by many different genres including country, pop and rock ’n’ roll. Everything was blending as she searched for what sounded like her—and what made Hailey James the artist she was becoming.
The search ended with her third single, Wide Awake, a song that earned Hailey Song of the Year from the MCMO and still is her most streamed song. “That song felt like me,” she says. “My producer and I focused on creating something unique that didn’t sound like anyone else. It sounded like me.”
Hailey James takes the stage alongside country music singer Dustin Lynch at Treasure Island Resort and Casino on July 24. Photo: David Sherman
Now, at 23 years old, Hailey continues to grow her career by earning Female Vocalist of the Year for the third time from the MCMO, signing with an agency and performing at Nashville’s iconic Bluebird Café, to name a few accomplishments. She’s also sung at U.S. Bank Stadium, shared a stage with country music singer Dustin Lynch and opened for none other than Underwood.
For Julie, seeing Hailey’s success has been nothing short of extraordinary. “I am so proud every time I see her onstage because I know the blood, sweat and tears that goes into the demanding lifestyle she has chosen,” she says. “It is a tough industry, and there are a lot of ‘no’ answers and disappointment that comes along with it. Fortunately, she has had a lot of success that … fuels her to keep moving forward and persevering.” AJ shares a similar sentiment. “I’m super proud. How could you not be when your kid is a rockstar?” he says.
The sound of Hailey James’ music is best described as a blend of country, pop and rock ’n’ roll. Photo: Chris Emeott
“It’s crazy to think how far I’ve come since I was 14,” Hailey says. “I want to help empower others [to] feel confident in their worth … When girls come up to me and say they want to be like me and do what I do, that means everything. I was that girl once.”
If Hailey could deliver a message to her 14-year-old self, she says she would love to tell the girl who was once nervous on stage that she can’t let self-doubt ever get in the way. “It takes time and work, and it won’t happen overnight,” she says. “But it will be the most rewarding thing you do.”
The TB1Fund Summer Sounds Festival in Ham Lake benefits M Health Fairview Masonic Children’s Hospital. Hailey James performed at the festival on July 12, 2025. Photo: Julie Trzebiatowski
Hailey James
Instagram: @haileyjamesmusic
