JACKSON, Wyo. — Million Dollar Music Fest on Old West Days weekend returns for its sixth annual edition, a delightful community offering of free country music to kick off summer in Jackson Hole.

Some locals are jokingly referring to this as the Million Dollar Midland Fest, as the Texas trio Midland has been a staple on the bill for numerous years. But the band continues to rise in popularity and demand in its 10th year, and free is no joke when it comes to producing concerts of this size with this level of talent, on Town Square, no less. The Grammy-nominated trio has a strong connection with forming the group in Jackson Hole. Their sound is genuine, they have solid traditional-meets-modern material, the harmonies are spot-on and they have aptly honed modern country performance as a headlining act for this size festival. Their most recent album is 2024’s “Barely Blue,” with more recent live releases highlighting songs at Red Rocks.

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Honkytonk hit-maker and romantic balladeer, Kentuckian John Michael Montgomery brings the sound of golden era ’90s country. Just give a spin of “Sold” or “I Swear” to be transported a couple of decades. Get ready for a load of chart-topping hits. 

With a striking and cutting vocal delivery, Canadian Tenille Townes will open the show. She was a featured songwriter at the 2024 Cowgirls at the Cowboy Showcase last fall and she’s an endearing storyteller with strong material, including several co-writes with her hero and decorated Nashvillian, Lori McKenna.

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The 6th Annual Million Dollar Music Fest featuring Midland and John Michael Montgomery with special guest Tenille Townes, Sunday, May 25 on Jackson Town Square. Gates open at 4 p.m. All-ages. VIP tickets sold out. Rain or shine event.

* John Morgan will play a festival kick-off show, 8 p.m. on Friday May 23 at the Million Dollar Cowboy Bar. Tickets start at $25/GA, $100/reserved seating.

* Ashley Wineland will play at 8:30 p.m. on Saturday and Sunday at the Million Dollar Cowboy. Tickets TBD.

Aaron Davis is a songwriter, multi-instrumentalist, vocalist, and producer-engineer at Three Hearted Recording Studio in Hoback, covering the Teton County music scene as a journalist-photographer since 2005.