Key West Songwriters Festival marks 30 years with 150 artists

The 30th Key West Songwriters Festival is set to close part of Duval Street and Greene Street for its free downtown concert, turning the Southernmost City into a weeklong stage that reaches far beyond one venue and into the island economy.

The festival says it is the largest of its kind in the world and is marking its 30th year with five days and nights of live music and storytelling from more than 150 artists across Key West. That spread matters in a city where the show does not stay in one arena. It moves through intimate indoor rooms, outdoor stages, bars and restaurants, pulling crowds into places that depend on steady foot traffic as much as on headliners.

The city of Key West calendar lists the free Duval Street concert for Saturday, May 2, 2026, from 6:30 p.m. to 11 p.m. It also says the 100 to 200 blocks of Duval Street and Greene Street between Fitzpatrick and Ann streets will close at 6 a.m. that day for setup, a sign of how much downtown changes when the festival hits its peak.

This year’s lineup includes DJ Smoke, Cody Lohden, Ashley Cooke and Ernest on the free street concert bill. Cooke stands out as one of country music’s most closely watched young storytellers. Her official bio says she broke out in 2023 with shot in the dark, then landed her first country radio No. 1 with your place, a gold-certified, Billboard Hot 100-charting hit that later won a 2024 CMT Music Award for Breakthrough Female Video of the Year. Her site also notes nominations from the ACM Awards and the iHeartRadio Music Awards, along with a recorded collaboration with Joe Jonas.

For Monroe County, the festival lands in the middle of a tourism economy that does much of the county’s heavy lifting. The county’s fiscal 2025 annual report says visitors spend about $3.5 billion a year in the Florida Keys, generating almost $400 million in tax revenue and supporting more than 24,000 local jobs in an island chain with about 80,000 residents. In that setting, a music festival is not just a cultural marker. It is a direct boost to hotel rooms, bar tabs, restaurant checks and side-stage venues that keep the local economy moving.

After three decades, the festival has become both a calling card and a business engine for Key West, drawing recognizable names like Kacey Musgraves, Florida Georgia Line, Jake Owen, Michael Ray, Randy Houser and Maren Morris while helping fill the calendar, and the cash registers, across Monroe County.