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05/25/2025 - 5:00pm to 10:00pm
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Concerts and Entertainment in Jackson Hole

Don’t miss the legendary Midland with John Michael Montgomery and Tenille Townes on the Jackson Hole Town Square!

On Sunday May 25th, Midland will make a triumphant return to the Million Dollar Music Fest and the town of their roots. The multi-platinum, GRAMMY-nominated trio will bring their neotraditional blend of toe-tapping honkytonk and genre-bending country to Town Square for their first Jackson Hole appearance in three years.

Making his Jackson Hole debut, John Michael Montgomery, another multi-platinum recording artist, with seven Country Music Association and Academy of Country Music awards, will bring his nineteen Top-5 hits, including seven #1’s to the Million Dollar Music Fest stage as part of his Road to Home Farewell Tour.

Opening the show, fresh off her own sold-out headlining tour of Canada will be Tenille Townes, who made her Jackson debut at the 2024 Cowgirls at The Cowboy. Winner of two ACM awards and an astounding 15 Canadian Country Music Association Awards (including five times as Female Artist of the Year and one Entertainer of the Year), Townes will bring her country rock style that owes as much to Janis Joplin as Miranda Lambert. Cowboy Bar darling, Ashley Wineland will perform immediately following the show at the after-party inside The Cowboy Bar, beginning at 9 pm.

FREE OUTDOOR CONCERT
Gates will officially open at 4:00 p.m. for this rain-or-shine concert event. The show is free to the public.

While the show is free, a limited number of VIP tickets will be available for purchase and will include prime, side-line viewing with access to a complimentary bar and food, private restrooms and a souvenir lanyard. VIP Tickets are available for purchase, click here to learn more!

For the general public, beer, wine and food will be available for purchase inside the grounds.