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Festivals & events · Key West

Festivals & events in Key West

Festivals, fairs, shows and one-off events on in Key West this week.

7 picks · 3 free · updated 19 October

NightlifeEat & drinkTours & day tripsArts & cultureOutdoors
Fantasy Fest 2026: Musical Icons and Iconic MusicalsMon 19 October · Old Town Key West33rd Original Homemade Bikini ContestWed 21 October, 7pm · Irish Kevin's · From $20FreeFantasy Fest Street Fair and Costume PromenadeFri 23 October, 12pm · Duval StreetFreeCaptain Morgan's Masquerade MarchFri 23 October, 5:30pm · Frances and Petronia Streets to Duval StreetFantasy Fest Parade Viewing Party at First FlightSat 24 October, 6pm · First Flight Island Restaurant & Brewery · From $125Mangoes Fantasy Fest Parade PartySat 24 October, 6pm · Mangoes Restaurant · From $90FreeDeep Eddy Vodka Fantasy Fest ParadeSat 24 October, 7pm · Duval Street
What’s On Key WestEverything on in Key West this weekThe Top 10, tonight, food, walks and nights out.For hotels & hostelsRun something in Key West?Hotels and hostels on FreeGuides list their events, tours and favourite places here for free.

Festivals & events in Key West, answered

What are the best festivals & events picks in Key West?

Right now: Fantasy Fest 2026: Musical Icons and Iconic Musicals, 33rd Original Homemade Bikini Contest, Fantasy Fest Street Fair and Costume Promenade and Captain Morgan's Masquerade March. The list is refreshed several times a day from FreeGuides' own research.

Are any of them free?

Yes: Fantasy Fest Street Fair and Costume Promenade, Captain Morgan's Masquerade March and Deep Eddy Vodka Fantasy Fest Parade.

Can I plan a day around these?

Yes. Open What's On Key West and use Plan my day: it builds a day from these and everything else on in Key West, with a link to book each one. Ask Eli, FreeGuides' trip planner, to plan several days.