Every festival, every parade,
every excuse to party.
Key West has a national-caliber festival nearly every month. We track the ones worth flying for and tell you when to book your hotel months ahead.
Last updated August 2026Dates are compiled from each event's official page — tap an event to confirm on the source.
Mile 0 Fest
Texas red-dirt + Americana songwriter festival at Truman Waterfront. 4 days, 40+ artists.
Key West Food & Wine Festival
5 days of tastings, dinners, and pairings across 30+ KW restaurants.
Key West Race Week (Quantum)
Premier mid-winter regatta. Spectator-friendly from Mallory Square.
Goombay Festival (Bahama Village)
Bahama Village street festival on Petronia Street — music, food and island culture, on the first day of Fantasy Fest.
Zombie Bike Ride
Costumed group bike ride, part of Fantasy Fest week.
Fantasy Fest
Ten days of costume parties and parades; 2026 theme "Musical Icons and Iconic Musicals". Parade Sat Oct 24, 7pm on Duval. Some evening events are 18+ or 21+.
Key West World Championship Offshore Powerboat Races
Offshore powerboat world championship week in Key West. Check the organizer's schedule for race days and viewing spots.
Key West Film Festival
The 15th annual festival of film screenings and events around Key West.
Key West Lighted Boat Parade
The 35th annual parade of lit-up boats around the harbor; the judges' stand is at Schooner Wharf.
Bight Before Christmas
The Historic Seaport's holiday lighting of the Harborwalk; in 2025 it started on Thanksgiving Eve and the lights stayed up through New Year's Eve.
Key West Home Tours (Old Island Restoration Foundation)
The 67th annual tour of five historic Key West homes, docent-led and self-paced. Tickets $45 members / $55 non-members (organizer, checked Oct 2, 2026).
Key West New Year's Eve drops
Three midnight traditions on and near Duval: the 33rd conch shell drop at Sloppy Joe's (Duval & Greene, no cover, first come), the 29th high heel shoe drop at Bourbon St Pub (724 Duval), and the pirate wench lowering at Schooner Wharf.
See our Key West tips and event updates more often when you search Google.