WEBCAMS
Jackson, WY – Every May, the spirit of the West rides high in Jackson Hole—and in 2025, Old West Days promises to be more vibrant than ever with a full lineup of live music that blends cowboy roots with country rhythms. From high-energy concerts on the Town Square to intimate sets at legendary venues like the Million Dollar Cowboy Bar, the music of Old West Days is more than background noise—it’s the beating heart of the celebration.
At the center of it all is the Million Dollar Music Fest, returning on Sunday, May 25, as the marquee event of the weekend. Presented by The Cowboy Bar and a signature event of Old West Days, presented by the Jackson Hole Chamber of Commerce, this free, all-ages outdoor concert transforms the historic Town Square into a stage for award-winning country stars, rising talent, and local favorites—all in celebration of Jackson Hole’s Western heritage.
Headliner Acts Bringing the West to Life
The 2025 Million Dollar Music Fest boasts a star-studded lineup that reflects the range and richness of today’s country music:
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Midland – The GRAMMY-nominated, multi-platinum trio returns to Jackson Hole with their signature honkytonk-meets-modern-country sound. This is their first performance in Jackson in three years, and fans are ready to welcome them back with open arms.
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John Michael Montgomery – Country royalty takes the stage for his Jackson Hole debut on the Road to Home Farewell Tour. With 19 Top-5 hits and 7 number-one singles, Montgomery is sure to deliver a night of nostalgic chart-toppers and heartfelt ballads.
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Tenille Townes – Known for blending the soul of Janis Joplin with the grit of Miranda Lambert, Townes is back in Jackson after her sold-out show at Cowgirls at The Cowboy. With 15 Canadian Country Music Association Awards and an ACM win under her belt, she’s a rising star with serious staying power.
Kick-Off Shows, After-Parties & More
The Million Dollar Music Fest is the centerpiece, but music flows all weekend long:
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Kick-Off Show: The weekend gets rolling with rising star John Morgan performing live at the Million Dollar Cowboy Bar, one of the West’s most iconic venues.
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Million Dollar After-Party: When the Town Square stage goes quiet, head back to The Cowboy for an intimate and electric set by Ashley Wineland, a local favorite who brings just the right mix of country soul and Western flair.
These shows are part of a larger Old West Days music lineup that fills the valley with sound—from fiddle tunes and acoustic sets to big-name acts under the stars.
More Than Just a Concert Series
The music of Old West Days brings people together from all walks of life to celebrate Western traditions and cowboy culture through shared experiences. Whether you're swaying to a ballad, two-stepping with a partner, or singing along to your favorite hit, these performances help tell the story of Jackson Hole’s heritage—loud and proud.
“This festival is more than just a concert—it’s a true celebration of Western heritage and cowboy culture,” says John Morgan, Director of Events & Communications at the Jackson Hole Chamber of Commerce. “We are proud to have such an incredible event be a part of Old West Days, where locals and visitors alike can come together to kick off the summer season in true Wyoming style.”
Mark Your Calendar: Sunday, May 25, 2025
Whether you’re a local looking for your favorite annual tradition or a first-time visitor ready to experience Jackson Hole in full swing, the Million Dollar Music Fest and the broader Old West Days music scene offer something unforgettable.
Get ready to two-step into summer—right in the heart of the Tetons.
Learn more about the full music lineup and event schedule at: jacksonholechamber.com/old-west-days/music