May in the Keys: Songwriters, Mahi Tournaments, and the Shoulder Season Sweet Spot

Ask a Conch their favorite month and half of them will say May. The snowbirds are gone, hotel rates drop, the water hits 80 degrees, and the summer thunderstorm machine has not switched on yet. It is the last deep breath before hurricane season.

It also happens to be packed. Here is your May 2026 rundown.

1. Key West Songwriters Festival (Apr 29 to May 3)

The 30th annual, and the biggest songwriter festival in the world. Something like 150 Nashville writers playing intimate rounds across 30+ Key West venues for five days. The songs you hear on the radio, performed by the people who actually wrote them, in a bar that holds 80 people.

• Local Tip: Skip the ticketed headliners. The magic is the free afternoon rounds at waterfront bars, and most of them need no wristband at all. The Duval Street street concert is the big free blowout. Do not even think about parking downtown. Bike.

2. I.CARE Trash Derby and Festival (Apr 30 to May 3)

Islamorada's annual reef cleanup: divers haul discarded traps, line, and debris off the reef all weekend, then everyone celebrates at Founders Park with live music and local food. Tourists mostly do not know this exists. Locals run it.

• Local Tip: If you dive, volunteer. If you do not, the Founders Park finale is free and family-friendly, and the dive-boat stories at the after-party are worth the trip alone.

3. Marathon Offshore Bull and Cow Dolphin Tournament (May 1 to 3)

Peak mahi season means a $20,000 guaranteed payout for the biggest bull-and-cow combined weight out of Marathon. Not fishing? The weigh-ins at the host marina are where the storytelling happens. May is when every freezer in the Keys gets restocked with mahi.

4. KEYS100 (May 16 to 17)

One hundred miles on foot from Key Largo to Key West, down the shoulder of US-1, over the bridges, in the heat. There are 50-mile and 50K options for the slightly more sensible.

• Local Tip: You will experience this mostly as runners and pacers on the highway shoulder all Saturday. Give them room on the bridges. The Sunday finish-line scene at Higgs Beach is free and weirdly inspiring to watch with a coffee.

5. Schooner Wharf Minimal Regatta (Sun, May 24)

Memorial Day weekend at the Historic Seaport. Teams build boats out of plywood, duct tape, and optimism, then race them in the Bight. Many sink. Sinking is part of the scoring, spiritually if not officially. Get there by late morning for a deck spot.

The May Short List

• Key West Paddle Classic (around May 9, verify day-of): a 12-mile paddle around the island. Serious athletes, beautiful course.
• Morada Way Art Walk (Thu, May 21, 6 to 9pm). Summer edition: smaller, more local, better.
• Key West Theater has a solid month: George Thorogood with the Marshall Tucker Band (May 9) and 10,000 Maniacs (May 10).
• Stone crab season ends May 15. Final call until October.
• Sea turtle nesting season starts this month. If you live near the beach or you are renting a place that is, lights out on the shore side after dark. The hatchlings will thank you.

Memorial Day weekend (May 23 to 25) is the one genuinely busy burst: the Minimal Regatta Sunday, the ceremony at Truman Waterfront Monday at 11am. The rest of the month is ours. Enjoy it.