Ashley Wineland Kicks Off Memorial Day Weekend at the Cowboy Bar

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Get ready, Jackson Hole, Memorial Day weekend just got a serious dose of country sass.

Ashley Wineland, the boot-stompin’, whiskey-sippin’, red-white-and-blonde country artist from Arizona, is riding into town for a one-night-only performance at the Million Dollar Cowboy Bar on Friday, May 24th.

Wineland is known for her powerhouse vocals, no-nonsense lyrics, and the kind of stage presence that could make a taxidermied elk head nod along. Her patriotic anthems and heartfelt ballads are the perfect kickoff to Memorial Day weekend in Jackson Hole, when locals and visitors trade ski poles for fishing rods and swap snow boots for cowboy boots.

Here’s what you can expect:

  • Rowdy country tunes
  • A crowd ready to dance
  • That perfect Jackson blend of small-town charm and big-time talent

And let’s not forget what Memorial Day weekend is all about: honoring those who served. Ashley’s music often pays tribute to American values and the people behind them, making her show a good time and a fitting way to start the weekend.

So whether you’re rolling into town for a long weekend or just moseying downtown for the night, make your way to the Cowboy Bar and raise a glass to freedom, live music, and a country weekend well spent.

🎟 Friday, May 24
🏛 Million Dollar Cowboy Bar
🎤 Ashley Wineland takes the stage
🕘 Doors at 8 PM, showtime shortly after
🪩 Dancing mandatory (well… strongly encouraged)

The Old West Days Festival coincides with Memorial Day activities in Jackson. Do not miss the Million Dollar Music Fest Saturday, May 25th at the Cowboy Bar!

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