Key West Songwriters Festival Returns For 30th Anniversary With 200 Artists, Islandwide Performances
Five-day event blends concerts and storytelling, spotlighting rising stars and hitmakers.
KEY WEST, Fla. — The Key West Songwriters Festival will mark its 30th anniversary April 29 through May 3, bringing more than 200 songwriters to stages across the island in a five-day celebration of music and storytelling.
Presented by BMI and hosted by the Florida Restaurant & Lodging Association and Rams Head Presents, the festival transforms bars, beaches and historic venues into intimate listening rooms, offering fans a behind-the-scenes look at the stories behind some of country music’s biggest hits.
Organizers say the festival has built a reputation as a launching pad for artists on the brink of stardom. Before becoming household names, performers including Chris Stapleton, Kacey Musgraves, Luke Combs, Morgan Wallen, Kane Brown, Thomas Rhett and Walker Hayes all appeared at the event. More recent performers have included Carter Faith, Riley Green and Ella Langley.
This year’s lineup features a mix of established and emerging artists, including Ashley Cooke, HARDY, Jack Ingram, Robert Earl Keen, Lori McKenna, Liz Rose, Brian Kelley, Chuck Mead, Rissi Palmer, Bruce Robison and Robert Randolph.
The festival opens April 29 with a kickoff party at Sunset Pier at Ocean Key Resort & Spa, where Jeffrey Steele and The Brummies are scheduled to perform. On May 2, ERNEST will headline the festival’s free Duval Street block party, turning the city’s main corridor into an open-air concert venue. The event concludes May 3 with “Sunday Songs: Music & Mimosas” at Williams Hall.
Rams Head Southernmost Bar & Restaurant will serve as festival headquarters, hosting performances throughout the week and anchoring activity across the island.
The event’s legacy is closely tied to its community of returning songwriters. Bob DiPiero first performed at the festival in 1997, followed by Jeffrey Steele in 1998 and Chuck Cannon and Tia Sillers in 2000. James Slater has appeared every year since 2004, reflecting what organizers describe as a strong sense of continuity and creative collaboration.
Since acquiring the festival in 2021, Rams Head Presents has expanded its reach while maintaining its focus on songwriter-driven performances. Sponsors for the 30th anniversary include Gallagher, HD Radio, Texas Roadhouse, Dulce Vida Tequila, Empress Gin, Ketel One, Captain Morgan and Bud Light.
Visitors attending the festival can expect events throughout Old Town, with lodging options such as Pier House Resort & Spa, known for its ties to Jimmy Buffett’s early career, and La Concha Key West, which is celebrating its 100th anniversary this year and sits in the center of the Duval Street corridor.
Dining options highlighted during the festival include One Duval, Perla, Tropicado and Harbour View Cafe, offering a range of coastal and Caribbean-inspired cuisine.
Beyond the music, attendees can explore local attractions including the Chart Room Bar, Mallory Square’s nightly Sunset Celebration, the Ernest Hemingway Home and Museum and waterfront venues throughout the island.
Festival organizers said the event continues to offer a unique experience, combining live performances with personal storytelling in settings that bring audiences closer to the artists behind the music.
Additional information, including tickets and a full schedule, is available at keywestsongwritersfestival.com.