Key West · Late April
Key West Songwriters Festival
The Key West Songwriters Festival bills itself as the largest event of its kind anywhere: five days, more than 200 songwriters and over 60 shows spread across bars, theaters and waterfront stages in Old Town. These are not cover bands. They are the Nashville writers who penned the songs you know from the radio, playing them the way they were written and telling the stories behind them.
The festival marked its 30th year in 2026, running April 29 through May 3. Dates for 2027 have not been locked in yet, but the pattern holds steady: five days, Wednesday through Sunday, wrapping up the first weekend of May. The lineup usually drops in February.
Quick Facts
- When
- Late April into the first weekend of May, five days
- Where
- Venues across Old Town Key West
- Cost
- Most shows free; headliner shows and sunset sails ticketed
- Scale
- 200+ songwriters, 60+ shows
- Presented by
- BMI, produced by Rams Head Presents
- Since
- Mid-1990s; 30th annual in 2026
What makes it different
Most music festivals sell you a big stage and a distant view. This one puts you ten feet from the person who wrote a number one song, in a bar, for free. Writers play "in the round," trading songs and telling you what was actually going on when they wrote them. Hearing a stripped-down version of a song you have heard a thousand times on the radio, from the person who made it up, is the whole draw.
The festival started in the mid-1990s, driven by Charlie Bauer, the founding manager of Hog's Breath Saloon who later owned Smokin' Tuna. BMI came aboard as presenting sponsor in 1997 and the thing has grown every year since. It is now produced by Rams Head Presents, the crew behind the Key West Theater.
Where the shows happen
Shows run all over Old Town: Smokin' Tuna Saloon, the Key West Theater, Sloppy Joe's, outdoor stages on Duval, sunset sails out of the harbor, and the big ticketed nights at Coffee Butler Amphitheater on the Truman Waterfront. Everything is walkable. Do not bother with a car.
- · Free bar shows fill up fast. Get there at least 30 minutes early for the small rooms.
- · Ticketed shows at the theater and amphitheater sell out. Buy when the lineup drops, usually February.
- · Sunset sail shows are the sleeper pick: a schooner, a songwriter and a Gulf sunset.
- · Old Town rooms book out months ahead for this week. Reserve early.
Planning your trip
Late April and early May is one of the best windows of the year in Key West. The winter crowds have thinned, the summer heat has not fully arrived, and the water is warm enough to swim. Build in a free afternoon or two, because the best festival moments tend to be the unplanned ones: wandering into a bar at 2 p.m. and finding a writer with three Grammys playing to forty people.
Want more on Key West Songwriters Festival?
Official details from the organizers, plus Keys Weekly's coverage from the newspaper.
Frequently Asked Questions
When is the next Key West Songwriters Festival?
Dates for 2027 have not been officially announced. The festival runs five days ending the first weekend of May; the 2026 edition was April 29 to May 3. Watch keywestsongwritersfestival.com for the announcement, usually in winter.
Is the Key West Songwriters Festival free?
Most of it, yes. The bar and street shows are free to walk into. Headliner shows at the Key West Theater and Coffee Butler Amphitheater, plus the sunset sails, are ticketed.
Who plays the festival?
More than 200 songwriters, heavy on the Nashville writing community. These are the people who wrote hits for major country and pop artists, playing their own versions and telling the stories behind them.
Where should I stay?
Old Town, if you can. Every venue is within walking distance of Duval Street, and rooms in that pocket sell out months before festival week.
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