July 10 โ July 12, 2026 ยท 21 events
This weekend in Key West, Florida brings 21 live events across the city โ from music to comedy. 21 events are free. Here's what's on.
Key West may be the most reliably live-entertainment-dense town in America โ Duval Street alone offers more stages per block than most cities' entire downtowns. Sloppy Joe's carries its Hemingway-era legend with bands playing day and night, while the Green Parrot, a locals' institution since 1890, books some of the best roots and funk acts to make the drive down the Overseas Highway. Every evening, Mallory Square's sunset celebration turns street performance into civic ritual. Fantasy Fest each October is the island's gloriously unhinged answer to Mardi Gras, and Hemingway Days each July celebrates the island's most famous resident with readings, contests, and general mischief.