As the nation’s only all-female country festival returns to Jackson Hole for its fifth year, Cowgirls at the Cowboy will feature a legend of the genre taking the stage at the iconic Million Dollar Cowboy Bar.
Cowgirls at the Cowboy is annually organized and curated by Nashville-based singer songwriter Jenny Tolman, an artist who has built her identity on humor, sass, and southern charm. Her dedication to shining a light on women’s voices in country music has seen the festival successfully move into its fifth year, attracting both local audiences and gaining national recognition. This year, Tolman has done something remarkable with the lineup - combining legendary with rising stars.
“I feel so honored that I get to be a part of the creation of this festival. It was the brainchild of the late owner of The Million Dollar Cowboy Bar, and I am so grateful that he entrusted me to seek out the incredibly talented women of country music, and get to bring them out to the most beautiful spot in the country!” Tolman told Wyoming Sounds ahead of the festival.
Cowgirls at the Cowboy is kicking off on Thursday night with a Songwriter Showcase featuring female writers that have been telling the stories of Nashville for decades. Jessi Alexander is one of the most celebrated songwriters in Music City, having penned the iconic track “The Climb” for Miley Cyrus and racked up CMA, ACM and NSAI awards for hits for country-pop stars like JellyRoll, Megan Moroney, Lee Brice and Black Shelton. Alexander’s catalogue has been shaping country music from its capital to its audience further afield.
Joining her on the songwriter stage will be Maui-born Lily Meola following her breakout year that saw the release of her debut album Lucky to Be. The indie-country up-and-comer’s music is reminiscent of the outlaw heroes that characterised the West, making Cowgirls at the Cowboy the perfect stage. “It’s absolutely wonderful to celebrate women in music.. I’m beyond excited to get to play but might be even more excited to get to enjoy the other writers and artists!” Meola told Wyoming Sounds. “I was lucky enough to experience Jackson Hole once in my life before this and I’m honestly forever changed from that trip.. been dreaming of coming back ever since!”
The second night of the festival is taking it up a notch with full-bands entering the honkytonk and accompanying two breakout artists. The Cowboy’s own Jenny Tolman will be highlighting music from her recent album Music City Mutt as she returns from an appearance on the CBS performance series The Road. With this marking her seventh year at The Cowboy, the crowd is set to be familiar with her impressively playful style.
Closing the night is current “talk-of-the-town” and 2026 ACM New Female Artist of the Year Nominee Mackenzie Carpenter. The I Wish You Would hit maker will be heading to Jackson Hole from being on the road with Riley Green and Jason Aldean. Having been hailed as the next big thing in country, Cowgirls at the Cowboy offers a unique chance to see Carpenter playing at one of the nation’s most loved venues.
While the lineup has already promised a festival of fun, female power, this year’s headliner is almost too good to be true. The 14-time Grammy winner and Billboard Century Award recipient Emmylou Harris will be performing in Jackson Hole for the first time in her incredible career spanning over 55 years. With over 25 albums to her name, along with collaborations and songwriting credits with artists including Gram Parsons, The Band, Linda Ronstadt, Bob Dylan, Dolly Parton and Johnny Cash, Harris is a certified legend in the genre. Having recently embarked on her Farewell Tour, this could mark her first and last performance in Jackson Hole.
“It feels unreal to have Emmylou headlining, this year.” Tolman explained. “As a young artist, I looked up to her so much, and continue to be so inspired by her, so the fact that she’s here, and we’re getting to show her Jackson Hole for the first time, as a performer, is beyond amazing!”
There’s no better time than this to visit the iconic Million Dollar Cowboy Bar as it’s soon to enter its 90th year. Tolman left us with her hopes for the future of the festival: “My dream for Cowgirls at The Cowboy is to continue to shine a spotlight on some of the greatest female talent in country music as well as grow it to a place where it’s something that people look forward to every year.”
Saddle up and find your way to Jackson Hole.
