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sunset event at mallory square with street performers and a crowd watching.

Where Life’s a Celebration

Upcoming Key West Events

Plan your stay around upcoming events in Key West, Florida

You’ve probably heard about the famous sunset celebrations at Mallory Square. But in Key West, our tendency to express our delight goes beyond this nightly event. For example...

Leave your inhibitions behind for Fantasy Fest, a 10-day October extravaganza of elaborate costumes and all-night carousing. If beards are your thing, check out Hemingway Days, where Hemingway fans and lookalikes celebrate the author at all his former haunts. Attend the Parrot Heads Annual Meeting of the Minds, a festival celebrating Jimmy Buffet, if music is what stirs your soul.

If you’re the active type, we’ve got a race for that. From a seven-mile bridge run to mock-marathons, with prizes for best costumes, of course.

We’ve got festivals lauding lobsters, pole vaulting, competitive barracuda fishing and shell blowing. There’s Womenfest. Pridefest. There’s the Smallest Parade in the Universe, where all floats must come in under 18 inches long. Whatever you choose to celebrate, if it floats your boat, it floats ours too.

Sci-Fi Night Trivia

Friday, November 17 | 6PM - 8PM

Join us for an extraordinary night that will transport you to galaxies far, far away. Our themed trivia night is designed to challenge even the most seasoned sci-fi lovers. You'll find a vibrant atmosphere filled with excitement, camaraderie , and trivia prizes, while enjoying delightful food and drinks.


Sci-Fi Trivia Night at Winslow Bungalows Flyer with star, moon, planet, and spaceship illustrations