Key West Events
What's happening in Key West
Key West gets its own region for a reason. MM 0 to 9, but practically: an island with its own personality and the densest event calendar in the Keys. Duval Street has live music every night of the year. The big annual stuff happens here. Hemingway Days in July, Fantasy Fest in October, the Goombay Festival the weekend before Fantasy Fest, the Sloppy Joe's Hemingway Look-Alike Contest, the Conch Republic Independence Celebration in April, the red shoe drop on New Year's Eve. Beyond the famous ones, there's a steady rhythm of First Thursday art walks, Pier House sunset celebrations, theater at the Red Barn and Waterfront Playhouse, and chamber stuff. If you can only check one region for what's happening tonight, this is the one.
Spotlight
Upcoming Events
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Check back soon for events across the Florida Keys.
Frequently asked questions
- What are the biggest Key West annual events?
- Hemingway Days in mid-July. Fantasy Fest the week ending the last Saturday of October. The Goombay Festival the weekend before Fantasy Fest. The Sloppy Joe's Hemingway Look-Alike Contest during Hemingway Days. The Conch Republic Independence Celebration in April. And the red shoe drop on New Year's Eve. Fantasy Fest is the wildest, Hemingway Days the most concentrated.
- Is Key West good for events year-round?
- Yes. Duval Street has live music every night. Fantasy Fest in October, New Year's Eve, and Spring Break are the busiest periods. Summer is hotter and quieter but never empty. May through August are the months locals reclaim the island.
