Upcoming Key West Events

Here is a look at great upcoming events in Key West this month

October 17 - 26, 2025 Key West

• Key West Fantasy Fest

Bedtime Stories & Magical Monsters" is the official theme for Fantasy Fest 2025, Key West’s annual multi-day costuming extravaganza in paradise. From October 17-26, revelers can explore an array of exciting events, including the the exuberant Goombay Festival in the streets, the Zombie Bike Ride, a Bedtime Stories and Magical Monsters-themed 5K run/walk, the Captain Morgan Masquerade March (aka “Locals Parade”), the Royal Coronation of the 2025 Fantasy Fest King and Queen, plus concerts, theater productions, the enchanting Key West Pet Masquerade, the 41st annual Headdress Ball pageant, and the world-famous Key West Fantasy Fest Parade on Saturday, Oct. 25.