Key West Songwriters Festival Returns for 30th Year with 200-Plus Artists

The Key West Songwriters Festival is marking its 30th anniversary with its largest ambition yet: more than 200 BMI multi-genre creators descending on the island from April 29 through May 3, 2026, for five days of performances spanning free outdoor stages and ticketed shows at intimate venues including the Key West Theater.

Presented by BMI with the Florida Restaurant & Lodging Association and Rams Head Presents, the festival opens Wednesday, April 29 with the Sunset Pier Kickoff Party at Ocean Key Resort & Spa, featuring Jeffrey Steele, who first played the festival in 1998, alongside the Brummies. Rams Head Southernmost Bar & Restaurant will serve as event headquarters throughout the week.

The headliner roster already confirmed includes Ashley Cooke, HARDY, Brian Kelley, Chuck Mead, Rissi Palmer, Bruce Robison, and Robert Randolph. They will share stages with a deep bench of returning veterans: Bob DiPiero, who debuted in 1997 and helped build the event alongside founder Charlie Bauer; James Slater, whose consecutive run of appearances stretches back to 2004; and Ronnie Bowman, who will take the stage for his ninth straight year. Lori McKenna, Liz Rose, Rebecca Lynn Howard, and Phil Barton have all been fixtures since 2010. Jack Ingram and Lee Thomas Miller joined the roster in 2015, while Taylor Phillips, Aaron Raitiere, and Trent Tomlinson each made their mark in 2017.

The festival's signature free event, the annual block party at the Main Stage on Duval Street, is set for Saturday, May 2, with ERNEST serving as host. The week closes Sunday, May 3 with the return of "Sunday Songs: Music & Mimosas" at Williams Hall.

The milestone anniversary arrives with a track record that is difficult to overstate. Alumni who played Key West before breaking nationally include Chris Stapleton and Jamey Johnson in 2005, Thomas Rhett and Kacey Musgraves in 2011, Luke Combs and Kane Brown in 2016, Morgan Wallen and Ashley McBryde in 2018, and Ella Langley as recently as 2023. ERNEST, who first appeared at the festival in 2019, returns this year as a headliner and block party host.

BMI's promotional materials describe the event as the place "where Nashville charisma meets Key West charm," and the booking philosophy has long reflected that dual identity, mixing commercial country hitmakers with roots artists, emerging voices, and multi-genre writers across venues that range from amphitheater-scale to the kind of corner-bar stages Key West does best.

Full schedules and ticketing details are expected to be posted in March at keywestsongwritersfestival.com. Additional artists beyond the initial announced slate will continue to be revealed before the festival opens.