JACKSON, Wyo. — The unfortunate truth is that women are often excluded from performing at, let alone headlining, major country festivals. Now in its fourth year, the all-female Cowgirls at the Cowboy bucks this trend in a pioneering way, celebrating women artists right here in our backyard like no other venue in the country. The festival takes place Oct. 9 through Oct. 11 at the Million Dollar Cowboy Bar.
In what has become tradition at Cowgirls at the Cowboy, Thursday night is reserved for a sit-down, acoustic Songwriter Showcase, an in-the-round style show that has been common for decades in Nashville. Hear the artist’s hit songs and the stories beyond them. Nashville artist Jenny Tolman will once again host and perform at the event, accompanied by Willow Avalon and Trannie Anderson.
“A Southern belle raising hell,” Avalon is a Georgia native with a decidedly more roots-based sound, often void of the sugary country-pop that tends to dominate the Music Row conversations and Country Music Awards. That’s not to say she hasn’t gravitated from stripped back acoustic beginnings to full-band productions and country stompers. She has a quivering, distinctive voice and blends modern and outlaw country, Americana and rock.
A product of Waco, TX, Anderson is a CMA and ACM-nominated songwriter with more than 85 “cuts” by artists such as Lainey Wilson’s No. 1 hits “Heart Like a Truck” and “Wildflowers and Wild Horses.” Trading a life on the road as a touring artist for a Nashville-based lifestyle of a working songwriter, Anderson is accustomed to this intimate and conversational showcase format. In 2023, she was named “Breakthrough Songwriter of 2023” by Music Row, while the Nashville Songwriters Association International named her song “Heart Like A Truck” the Song of the Year.
Friday will up the decibel level with full-band sets and co-headlining performances from Tolman and Mae Estes. Currently on tour with Luke Bryan, Estes brings a contemporary sound, though also reminiscent of ’80s and ’90s country artists that had a simple and honest lyrical approach about everyday life. Tolman returns to the Cowboy for her sixth consecutive year. She’ll appear on the forthcoming Taylor Sheridan/Blake Shelton-produced CBS performance series, “The Road.”
Alabama native Ella Langley’s headlining appearance on Saturday at Cowgirls at The Cowboy will mark her debut Jackson Hole performance. From honky-tonk to modern pop-country and even a hip-hop collaboration, she’s a bold artist with smoky twang, rock grit and a bucket of accolades. After receiving eight nominations — more than any other artist at the 2025 Academy of Country Music Awards earlier this year — Langley took home five wins, including New Female Artist, Single, and Song of the Year. Her last two singles have reached No. 1 at country radio and achieved platinum status. In addition to her own sold-out headlining tour this year, she has toured in direct support of Riley Green and Morgan Wallen.
Though all-women festivals have somewhat grown in popularity in recent years — such as the 2024 Key Western festival in Key West with established artists like Wynonna, the 7th Annual Brandi Carlile-led Girls Just Wanna Weekend in Cancún, and the All Things Go festival celebrating female and LGBTQ+ artists — the Cowgirls at the Cowboy’s three-day event offers intimacy on a small scale with both up-and-coming artists and rising country stars. It also remains the only USA-based all-female event with an annual commitment.
Cowgirls at the Cowboy, 8 p.m. Thursday, Friday and Saturday (Oct. 9-11) at the Million Dollar Cowboy Bar. Doors at 6:30 p.m. each night. Saturday’s show is sold out, though tickets are still available for Thursday’s Songwriter Showcase ($100+) and Friday’s co-bill ($35+) at CowboyBarJH.com. Thursday will be fully seated, while the dance floor will be open on Friday and Saturday. 21+ only.
