The sixth-annual Million Dollar Music Fest, a highlight of Jackson Hole’s Old West Days, will bring free live country music to Town Square on Sunday, May 25, 2025, starting at 4 p.m. Presented by The Cowboy Bar, the event will feature headliners Midland, John Michael Montgomery, and opener Tenille Townes, celebrating Western heritage and cowboy culture. Midland, a GRAMMY-nominated trio, returns to their Jackson roots with neotraditional honkytonk, while Montgomery, on his Road to Home Farewell Tour, will perform 19 Top-5 hits, including seven No. 1 singles. Townes, with 15 Canadian Country Music Association Awards, will deliver her country rock style, followed by an after-party with Ashley Wineland at The Cowboy Bar at 9 p.m.
A kick-off show on Friday, May 23, at The Cowboy Bar will feature rising star John Morgan, known for his Top-10 hit “Friends Like That” with Jason Aldean. Reserved seats cost $100, and general admission is $25. The family-friendly fest offers limited VIP tickets for an enhanced experience, available from April 30 at cowboybarjh.com. The event draws thousands to celebrate Jackson’s summer season. More details are at jacksonholechamber.com/old-west-days.
