Johnny Shockey had certain intentions when he established it for the 2019 Under The Big Sky Rodeo Round-up and Music Festival in Whitefish, Montana. In 2015, the rancher and CEO of Outrider's Present purchased a roughly 400-acre ranch to showcase Montana's summertime beauty, highlight a diverse group of vocalists, and preserve the land.

Near the little village sixty miles from the Canadian border, at the Big Mountain Ranch, twenty thousand music lovers flocked for the Under the Big Sky Festival. Every day for three days, there were rodeos, merchants selling anything from crafts to tattoos, and a wide variety of musicians you wouldn't normally hear on the radio.

Artists such as Lord Huron, Cody Jinks, Margo Price, Trampled by Turtles, Lainey Wilson, Morgan Wade, Midland, Zac Bryan, Hogslop String Band, and more enjoyed performing for fans against the gorgeous background of Glacier National Park. On the first night, the critically acclaimed Turnpike Troubadours performed as the featured act.

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