Key West Songwriters Festival to Feature 50-Plus Shows May 3-7

KEY WEST, Florida Keys — Featuring more than 250 performing songwriters including multi-genre singer/rapper Jelly Roll, fresh from his triple win at the Country Music Television Music Awards, the 27th annual Key West Songwriters Festival is to feature an unparalleled five-day experience for music fans.    

Audiences can savor everything from powerhouse country rock and blues to Americana Wednesday through Sunday, May 3-7, at more than 50 shows and jam sessions in island settings. Spearheaded by Rams Head Presents and international performing rights organization BMI, the festival has become a tradition for an incomparable group of writers and musicians. 

The 2023 lineup includes three-time Grammy Award nominee Elle King, country pop notable Mitchell Tenpenny, renowned southern writer Rivers Rutherford, prolific chart-topper Jeffrey Steele, former Mavericks frontman Raul Malo and the songwriting super-trio dubbed the Love Junkies. 

Events are to begin at 6 p.m. Wednesday, May 3, with a kickoff party and multi-artist show at the Ocean Key Resort’s Sunset Pier overlooking the Gulf of Mexico at 0 Duval St. Hosted by broadcaster Storme Warren, the performance is to star Robert Randolph with the Dylan Altman Blues Band as well as festival favorite James Slater. 

Anticipated highlights include a concert by Jelly Roll set for 8 p.m. Friday, May 5, at the Coffee Butler Amphitheater at Truman Waterfront, 21 E. Quay Road. With more than 24 albums to his credit including 2021’s “Ballads of the Broken,” Jelly Roll delves into genres ranging from country-tinged rock to rap.   

At 7 p.m. Saturday, a free “block party” performance is scheduled in the 200 block of Key West’s Duval Street. Hosted by Warren, the high-energy event is to be headlined by Michael Ray. 

Most of the festival’s shows feature a rotating group of writer/performers and many have no admission charge. Offerings are to be presented at island city bars, restaurants, resort beaches and poolsides as well as event headquarters, the Rams Head Southernmost Bar & Restaurant at 804 Whitehead St. 

In addition, ticketed group shows are to be staged at venues ranging from the San Carlos Institute, a Cuban cultural center at 516 Duval St., to the Fury Catamaran during an exclusive sunset cruise.

The most up-to-date event schedule can be found on the official Key West Songwriters Festival app, available through the Apple App Store or Google Play with direct links at keywestsongwritersfestival.com/copy-of-schedule. 

The festival concludes Sunday, May 7, after a day of live music capped by an 8 p.m. all-star encore at the Key West Theater at 512 Eaton St.

Presenter Rams Head Group, established in 1989, is a family-owned entertainment and restaurant company with operations in Key West and Maryland. 

Festival information, full schedule and ticketing: kwswf.com