The annual Million Dollar Music Festival will be staged over three nights inside the famous Jackson Hole venue. Photo: Courtesy of The Cowboy Bar

JACKSON HOLE, Wyo. — The Million Dollar Music Fest will return to Jackson Hole, WY this Memorial Day weekend with three exciting nights of headline entertainment on the stage of the iconic Million Dollar Cowboy Bar. The 2021 line-up features Jackson Hole favorites, Midland, Runaway June and Jenny Tolman. Tickets will be available beginning Tuesday, April 20 at 10 a.m. MST at

Photo: Runaway June

To headline and close out the 2021 Million Dollar Music Fest, on Sunday May 30, GRAMMY®- nominated country super-group, Midland, will return to the town where they first formed. Far from sitting idle during the shutdown, Midland recently debuted a film, The Sonic Ranch, and a soundtrack of unheard songs, which documents their genesis as a group. They’ve also been in the studio recording an album of all new music that will be released very close to their Jackson Hole return. This will mark their third commercial release, following On The Rocks, which reached #1, and Let It Roll, their second release which debuted at #1 on Billboard’s Top Country Album Sales chart. They have received near-unanimous praise from outlets as varied as Rolling Stone, Variety, NPR and Entertainment Weekly. The trio was nominated for New Artist and Vocal Group of the Year at the 2019 Country Music Association Awards, after winning at the previous year’s Academy of Country Music Awards. Bassist and founding member, Cameron Duddy said, “We are super excited to return to Jackson Hole. We view The Million Dollar Music Fest as a way for us to let the region know just how much it means to Midland, both individually and as a group. In many ways, Jackson feels like home.”

Rising stars, Runaway June, who, one year ago, played their first-ever sold-out headline show at The Cowboy, will return to its iconic stage to headline on Saturday May 29. Comprised of Naomi Cooke, Jennifer Wayne, and newcomer Natalie Stovall, Runaway June has quickly made their mark on the country music scene with their critically-acclaimed songwriting and tight-knit, three-part-harmonies. “Buy My Own Drinks,” the self-penned, lead single from their debut release, Blue Roses, became the first Top-5 radio hit by a country female trio in sixteen years. Since forming four years ago, these singer-songwriters have become a multiple- time Academy of Country Music and Country Music Television Award-nominated band, and were named CMT’s “Next Women of Country.” In the year of its release, Rolling Stone ranked Blue Roses #14 on its list of “The 40 Best Country and Americana Albums.” A highlight of their career so far was a 55-city tour of sold-out arena shows as a support act on the Carrie Underwood Cry Pretty Tour 360. “We are so honored and excited to be playing music once again in one of our favorite towns in the world, Jackson Hole,” said lead singer, Naomi Cooke. “The legendary Million Dollar Cowboy Bar holds a special place in our hearts. The hospitality, charisma, and unique personality this place holds is truly priceless and like no other. We are so pumped up and ready to be back on stage for the first time in a long time and we can’t think of a better place to do that.”

Photo: Jenny Tolman

In October 2020, Jenny Tolman headlined a sold-out Silver Dollar Showroom Session as a duet with her GRAMMY®-nominated partner Dave Brainard. On Friday, May 28, Tolman will bring her full band to kick off, in high style, The Million Dollar Music Fest at The Cowboy. Blending the songwriting styles of her influences Dolly Parton, Shel Silverstein and Roger Miller, Tolman’s debut release, There Goes the Neighborhood, takes the listener on a trip through the fictional town of Jennyville, full of what The Boot calls “color, comedy and poignant, incisive lyrics that paint a vivid portrait, where eccentric, vibrant characters live, and aren’t afraid to do-si-do around tender subjects, and call things like they are.” The album was included on numerous “Best of” lists, ranking #24 on Rolling Stone’s Top 40, ahead of such mainstays as Reba and Brooks & Dunn. Singles like “So Pretty,” “High Class White Trash” and “My Welcome Mat,” exemplify her quirky, tender and humorous style. In April she will digitally re- release There Goes the Neighborhood, featuring three new, unheard tracks.
After falling victim to the 2020 shutdown, event organizers were intent on finding a way to present live music at The Million Dollar Music Fest in 2021. Jim Waldrop, president of Silver Dollar Inc., (parent company of The Cowboy Bar) said, “Just as we’ve done with all of our music over the last year, these indoor shows will follow current state and local health guidance. They will be sit-down-only, with a limited capacity which will allow our guests to enjoy the immense talent we’re presenting while confidently remaining safe.” Tickets for each show will be sold by-the-table only. Barstools, Two-top and four-top tables will be available to the public beginning Tuesday, April 20th, at 10am (MT) and may be purchased online at

The Million Dollar Music Fest made its debut in 2019 on the historic Town Square of Jackson, WY, attracting more than five thousand people to the mountain town. The event, which is presented by The Million Dollar Cowboy Bar, and sponsored by the Jackson Hole Travel and Tourism Board, Jackson Hole Chamber of Commerce and Wyoming Whiskey, serves to energize Old West Days by celebrating Jackson’s western heritage and cowboy culture in grand Wyoming style. The Million Dollar Cowboy Bar, established in 1937, is widely regarded as a national treasure and is regularly named one of the top honkytonks in the country. Since buying it in January 2018, ownership is dedicated to returning The Cowboy to the iconic status it enjoyed when it hosted the biggest names in country music. #saddleup