Everything You Need to Know About the Key West Songwriters Festival

It wouldn’t be spring in Key West without the annual Key West Songwriters Festival (KWSF). This iconic festival - and largest of its kind in the world - honors over 200 veteran and up-and-coming artist-songwriters who write hits for country, folk, pop, blues, and rock’s hottest music billboard acts. For five days and nights, May 1 - 5, 2024, artists take over Key West venues, perform their original songs, and share the stories behind them.

The beauty of the KWSF is that it provides the chance to hear the songs you know and love in their most basic form. It’s also a great opportunity for songwriters to connect, network, and make a name for themselves. In fact, the festival has been credited with helping to launch artists like Kacey Musgraves, Florida Georgia Line, Jake Owen, Michael Ray, Randy Houser, and Maren Morris to superstardom.

Here’s everything you need to know about the 28th annual Key West Songwriters Festival, including dates, ticketing information, and the most anticipated events of 2024. Read on.

[Reserve your spot to the official Key West Songwriters Festival Pool Party]

Key West Songwriters Festival 2024 Dates

This year, the festival will run from Wed. May 1 through Sun. May 5, 2024.

Key West Songwriters Festival 2024 Location

KWSF is one of the liveliest times of the year in Key West and an excellent way to visit select venues all over the island. Musical acts will be performing at Key West mainstays like the Key West Theater, Blue Heaven, Irish Kevin’s, Schooner Wharf Bar, Green Parrot, Sloppy Joe’s, Conch Republic Seafood Co., and 24 North Hotel’s very own Sunset Green Event Lawn.

[Key West packs a lot of punch in its relatively small surface area. To keep tabs on Duval Street nightlife, seasonal seafood, event guides, and more, bookmark the 24 North Hotel Blog]

Key West Songwriters Festival 2024 Headliners, Lineup, and Schedule

Headlining this year’s festival is American country music singer-songwriter Cole Swindell, alongside acts Mackenzie Carpenter, Dallas Davidson, Robert Earl Keen, Dylan Marlowe, Lori McKenna, Robert Randolph, and Liz Rose. We’ve only included the hot ticket  headliner shows below, but check out the full Key West Songwriters Festival schedule here.

-Sunset Pier Kick Off Party with Dylan Marlowe, Heartwreckers, and Kristen McNamara; Wed. May 1; 6 - 8:30 p.m. at Sunset Pier. Free.
-‘In the Round’ with Lori McKenna, Taylor Phillips, Chase Matthew, Thomas Edwards, Lee Thomas Miller, Wendell Mobley, Bob DiPiero, and Luke Laird; Thurs. May 2; 4 - 7 p.m. at Key West Theater. Tickets.
-Cole Swindell with Restless Road and Mackenzie Carpenter; Thurs. May 2; 7 - 10:15 p.m. at Coffee Butler Amphitheater. Tickets.
-Robert Randolph Band with Chuck Cannon, Dylan Altman, and Guthrie Trapp; Thurs. May 2; 8 p.m. - 11:30 p.m. at Key West Theater. Tickets.
-‘In the Round’ with Robert Earl Keen, Lee Thomas Miller, and Wendell Mobley; Fri. May 3; 8 - 11 p.m. at San Carlos Institute. Tickets.
-Bloody Mary Bash with Robert Earl Keen and Friends; Sat. May 4; 10 a.m. - 12 p.m. at Key West Theater. Tickets.
-Dallas Davidson & Friends, Kaleb Sanders, and Lily Rose; Sat. May 4; 7 - 10 p.m. at Main Stage 200 Block of Duval Street. Free.
-Texas Heritage Songwriters Association and Texas Music Office Present - ‘San Carlos Institute Texas Showcase’ with Liz Rose, Garrett Bradford, Morgan Lee Powers, Robynn Shayne, Russell Sutton, Paul Jenkins, Scott Sean White, Jack Ingram, and Aaron Barker; Sat. May 4; 8 - 11 p.m. at San Carlos Institute. Tickets.

Best Events of Key West Songwriters Festival 2024

The five nights of the festival are stacked with stellar performances, but we think these events offer something extra special:

Kick off the Songwriters Festival and write a song with Rob Snyder and CreatiVets at the Sunset Green Event Lawn at 24 North Hotel. REV Up - Meet Up & Write will take place May 1, 1 - 5 p.m. Music provided by Andy Westcott Band Unplugged, James Slater, Rob Snyder, Jobe Fortner, and Ryan Nelson.

The Fury Catamaran is getting in on the festival action as well by hosting a Live Music Sunset Sail on May 2 and May 4 at 6 p.m. The sails feature live musical performances by KWSF artists, plus appetizers, margaritas, and a full liquor bar. Performers on the bill include the Grammy-nominated duo Thompson Square, Carlyle Griffin, and Barrett Baber.

Realign with Emma Klein on the Sunset Green Event Lawn on May 4 from 10 - 10:30 a.m. The 30-minute beginner yoga stretch with the budding singer-songwriter is the perfect way to recenter before you make your way back to the KWSF.

For a block party bash with the Key West community, check out the Songwriters Main Stage at the 200 Block of Duval Street beginning at 7 p.m. on Sat., May 4, hosted by radio broadcaster and "Dick Clark of Nashville," Storme Warren. The free show will star Dallas Davidson & Friends, Kaleb Sanders, and Lily Rose.

Next door at our sister hotel The Gates Hotel, the official Key West Songwriters Festival Pool Party will be held on May 5 from 1 - 4 p.m. (event flyer pictured above). The free event features live music, Dulce Vida tequila, good vibes, and poolside fun. Talented songwriters in attendance include Quake Matthews, Hueston, Sacha, Maggie Baugh, Vincent Mason, Matt Wynn, Andrew Beason, and Paul Jenkins. Reserve your spot here. 24 North Hotel guests have exclusive access to all grounds and amenities at The Gates Hotel, 24/7.

Key West Songwriters Festival 2024 Tickets

Many of the festival venues are free to enter and shows typically begin early in the afternoon before playing well into the night. Places like the Key West Theater, San Carlos Institute, and Coffee Butler Amphitheater will host the bigger names of the festival, so grab your Key West Songwriters Festival tickets to these events in advance. For unprecedented access to all the shows, check out the Platinum ticket option.

The Key West Songwriters Festival is a quintessential slice of Americana that meshes perfectly with the laid-back vibe of Key West. So get down to the KWSF, happening May 1 - 5, 2024, and pack your guitar, we’ve got just the space for it and plenty more for you at 24 North Hotel. Book direct to save up to 25% and see which of our special offers works for you.