Conch Republic Independence Celebration (Annually, week of April 23). Week-long festival commemorating the April 23, 1982 symbolic secession of Key West. Includes mock naval battles, costume parties, and events celebrating Key West's distinctive culture and identity.
Hemingway Days (Annually in late July (coinciding with July 21, Hemingway's birthday); 2026 dates: July 22–26). Annual festival founded in 1981 by Michael Walton at Sloppy Joe's Bar, honoring Ernest Hemingway's 12-year residency in Key West. Features the internationally known Hemingway Look-Alike Contest, Running of the Bulls,…
Key West Lobsterfest (Annually in August (first or second week); 2026 dates: August 5–9). Annual four-to-five day festival celebrating the opening of Florida Spiny Lobster season. Features a Duval Street fair, live music, chef dinners, lobster cook-offs, and a pub crawl. Proceeds benefit the Key West High…
Fantasy Fest (Annually in October (mid-to-late); 2026 dates: October 16–25). Ten-day adult costume festival held annually since 1979, centered on Duval Street. Key events include the Zombie Bike Ride, Headdress Ball, and the Grand Parade. The 2026 theme is 'Musical Icons and Iconic Musicals.'…
Goombay Festival (Annually in October (within Fantasy Fest period); 2026 dates: October 17–18). Two-day celebration in Bahama Village honoring Key West's Bahamian heritage. Features live music, Junkanoo parade, traditional Bahamian cuisine, and colorful costumed dancers.
Sunset Celebration at Mallory Square (Nightly, year-round). Nightly arts festival held every evening at Mallory Square Dock, dating to informal gatherings in the late 1960s and formally organized by the Key West Cultural Preservation Society in 1984. Features street performers,…