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Wyatt Flores, Old Crow Medicine Show Among Headliners For Mile 0 Fest

July 15, 2026/by Lorie Hollabaugh

The Mile 0 Fest Key West Festival is celebrating 10 years of songs, sun and fun with its biggest event yet set for January 26-30, 2027, showcasing the very best in red dirt, Americana and Texas country music as well as up-and-comers.

Cross Canadian Ragweed, Ryan Bingham, Wyatt Flores, Kaitlin Butts and Old Crow Medicine Show will headline the landmark 10th Anniversary celebration, along with Wade Bowen, 49 Winchester, William Clark Green, Stoney LaRue, Cody Canada & The Departed, Tanner Usrey, Jason Scott & The High Heat, Kevin Fowler, Roger Creager, Micky & The Motorcars, The Creekers, The Jack Wharff Band, The Droptines, Adam Hood, Walt Wilkins, Red Dirt Rangers, Drew Kennedy, Josh Grider and many more, with more artists still to be announced.

Unlike a traditional festival held inside a single venue, Mile 0 Fest takes over the entire island as more than ten stages come alive throughout Key West, from Truman Waterfront Amphitheater to the historic Key West Theater, intimate songwriter venues, iconic bars, waterfront locations and surprise pop up performances around town.

“Mile 0 Fest has never been just about booking great artists,” says Kyle Carter, Founder of Mile 0 Fest. “From the very beginning, our goal was to create an experience that people couldn’t find anywhere else. Over the last ten years we’ve watched complete strangers become lifelong friends, artists create unforgettable collaborations, and fans build annual traditions around this week in Key West. Celebrating ten years is incredibly meaningful because it’s really a celebration of everyone who has made Mile 0 Fest what it is today. We can’t wait to welcome everyone back for the biggest year we’ve ever had.”

Festival packages and passes go on sale this Friday (July 17) at 9 a.m. CST.

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Lorie Hollabaugh
Lorie Hollabaugh
Hollabaugh, a staff writer at MusicRow magazine, has over 20 years of music business experience and has written for publications including American Profile, CMA Close Up, Nashville Arts And Entertainment, The Boot and Country Weekly. She has a Broadcast Journalism and Speech Communication degree from Texas Christian University, (go Horned Frogs), and welcomes your feedback or story ideas at lhollabaugh@musicrow.com.
Lorie Hollabaugh
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https://musicrow.com/wp-content/uploads/2026/07/Untitled-July-15-2026-at-09.34.15-3.png 1080 1080 Lorie Hollabaugh https://musicrow.com/wp-content/uploads/2019/03/MusicRow-header-logo-Mar19B.png Lorie Hollabaugh2026-07-15 09:58:452026-07-15 09:58:45Wyatt Flores, Old Crow Medicine Show Among Headliners For Mile 0 Fest

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