Hold onto your Stetson, Jackson Hole’s country music bash is back and bigger than ever. The Million Dollar Music Fest returns for its sixth glorious year on Sunday, May 25, 2025, bringing serious heat to the heart of Town Square. As always, this completely free, open-air concert is the crown jewel of Old West Days, pairing cowboy culture with country chords for a night that’s as Wyoming as it gets.
🎶 The Lineup That’ll Have You Movin’
This year’s roster is stacked like a cowboy’s breakfast plate, with chart-toppers, legends, and rising stars sharing the stage:
- Midland – The GRAMMY-nominated trio that practically wrote the manual on modern honkytonk is coming home. Midland’s return to Jackson Hole, where they first lit a match on their now blazing career, is a full-circle moment. Expect sequins, swagger, and steel guitars.
- John Michael Montgomery – He’s got seven #1 hits and a voice that defined a generation of 90s country. Now, he’s riding into Jackson for the first time ever on his Road to Home Farewell Tour. If you’ve ever slow danced to “I Swear,” this is your moment.
- Tenille Townes – You heard her tear it up at last year’s Cowgirls at The Cowboy. Now she’s back to open the festival with her signature blend of fire, soul, and storytelling. Think Janis Joplin meets Miranda Lambert, with a dash of Canadian grit.
And because Jackson doesn’t know when to quit…
🎉 After-Party at The Cowboy Bar
When the sun sets and the amps cool off, Ashley Wineland picks things back up where it all began, inside The Cowboy Bar, the heartbeat of Town Square. Bring your boots, your buddies, and your best dance moves.
🎤 Kick-Off Show: Start the Party Early
Why wait until Sunday? Start your Memorial Day Weekend with a bang on Friday, May 23, at the Kick-Off Show inside The Cowboy Bar, featuring the raw, radio-ready sound of John Morgan. He’s penned hits for Thomas Rhett and Jason Aldean, and now he’s headlining your Friday night.
Kick-Off Show Tickets:
- Reserved Seating: $100
- General Admission (Dance Floor Open): $25
🎟 Tickets available starting Wednesday, April 30 at cowboybarjh.com
⭐ VIP Experience
Want the best view in the house and a little extra room for your whiskey tumbler? Snag one of the limited VIP tickets and elevate your festival night from rowdy to refined. You’ll still get all the dust and drama of Town Square—just with a little more elbow room.
📅 Save the Date
Million Dollar Music Fest
Sunday, May 25, 2025
Jackson Hole Town Square
Gates open: 4:00 PM | Rain or Shine | Free to the Public
Whether you’re a local or a wide-eyed visitor, the Million Dollar Music Fest is Jackson Hole’s unofficial start to summer, where the stars align, the guitars twang, and the whole town gets a little louder (and prouder).
See you under the neon elk antlers.
