The festival, produced by OhWook! Productions, has evolved from an ambitious local concept into a national staple, recently named the top music festival in the country by USA Today. Headliners for the 2027 anniversary include Cross Canadian Ragweed, Ryan Bingham, Wyatt Flores, and Old Crow Medicine Show, alongside a broad roster of Americana and Texas Country talent. Unlike conventional festivals confined to a single arena, the event utilizes over ten stages scattered across Key West, ranging from the Truman Waterfront Amphitheater to historic theaters and intimate local bars.
To mark its tenth year, organizers are expanding the festival footprint. The Reach Key West, Curio Collection by Hilton, joins the rotation as a new waterfront performance space, while enhanced amenities at the main amphitheater aim to elevate the guest experience. Founder Kyle Carter notes that the event’s longevity stems from its focus on community building, noting how the festival has fostered collaborations and lifelong friendships between artists and attendees alike. Kaitlin Butts, who performed at the inaugural festival, returns as a headliner, highlighting the event's commitment to supporting both emerging talent and established voices within the genre. Festival packages, which bundle lodging with exclusive access to songwriter sessions and sailing excursions, go on sale July 17.

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