Key West to soundtrack spring with 30th Annual Songwriters Festival

Platinum-selling country duo LOCASH performs before a packed Duval Street crowd on May 3, 2025, at the 29th Annual Key West Songwriters Festival in Key West. [Larry Blackburn/Florida Keys News Bureau]

The 30th Annual Key West Songwriters Festival, hosted by the Florida Restaurant & Lodging Association and Rams Head Presents, returns April 29 through May 3, transforming bars, beaches and historic venues into intimate listening rooms where the story behind each hit is as important as the melody.

[Photo by Mark Hedden/Florida Keys News Bureau]

Since its inception in 1996, the festival has earned a reputation for spotlighting artists on the brink of stardom. Long before their names filled arenas, Chris Stapleton, Kacey Musgraves, Luke Combs, Morgan Wallen, Kane Brown, Thomas Rhett and Walker Hayes all took the Songwriters’ stage. In recent years, rising talents such as Carter Faith, Riley Green and Ella Langley have followed the same path.

This year’s lineup upholds that tradition with more than 200 Broadcast Music Inc. songwriters—including Ashley Cooke, HARDY, Jack Ingram, Robert Earl Keen, Lori McKenna, Liz Rose, Brian Kelley, Chuck Mead, Rissi Palmer, Bruce Robison and Robert Randolph—performing across the island. Rams Head Southernmost Bar & Restaurant will serve as festival headquarters, anchoring the action with full-day performances and artist meet-and-greets.

[Photo by Larry Blackburn/Florida Keys News Bureau]

The festival opens Wednesday, April 29, with the Sunset Pier Kick Off Party at Ocean Key Resort & Spa, where Jeffrey Steele and The Brummies will set the tone as the sun dips below the Gulf. Festival-goers can then move on to historic bars lining Duval Street, where impromptu “round robin” songwriting sessions, known locally as “writers’ rooms,” allow attendees to hear new material in stripped-down settings.

On Saturday, May 2, ERNEST headlines the free Duval Street block party—an open-air concert that turns the island’s most famous thoroughfare into a high-energy showcase of emerging and established talent. The weekend culminates Sunday, May 3, with Sunday Songs: Music & Mimosas at Williams Hall, offering a laid-back finale of acoustic performances and brunch.

Festival organizers note that the event’s enduring appeal lies in its focus on craft over celebrity.

Robert Randolph lights up Sunset Pier during kickoff night, blending soul, rock and pure stage fire under the Key West sky. He returns for the festival’s 30th anniversary, April 29–May 3, 2026.

[Photo by Mark Hedden/Florida Keys News Bureau]

Many songwriters return year after year, a testament to the community spirit that fuels the event. Bob DiPiero first played in 1997; Jeffrey Steele joined the following year. Songwriters Chuck Cannon and Tia Sillers debuted in 2000, and James Slater has performed every year since 2004. Their dedication underscores the festival’s role as both creative incubator and homecoming.

Since acquiring the festival in 2021, Rams Head Presents has expanded its reach while preserving the authenticity that makes Key West unique.

Whether discovering the next breakout artist or gaining insight into the songs you already know, the Key West Songwriters Festival delivers an experience found nowhere else—where every chord, lyric and backstory resonates against the island’s sunset-streaked skyline.