Key West Event Calendar

Events

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  • Minimal Regatta

    Date(s): May 24, 2026Venue: Schooner Wharf BarCategory: Community / WaterfrontWebsite: https://schoonerwharf.com/

  • Salute to Service 5K Run & Walk

    Date(s): May 24, 2026Venue: The Marker ResortCategory: Sports / CommunityWebsite: https://visitfloridakeys.com/plan-your-trip/plan-book/events/salute-to-service-5k-run-walk

  • Burgers & Buffet Tunes

    Weekly Thursday tribute lunch show. Date(s): May 28, 2026Venue: Comedy Key WestCategory: Music / Lunch ShowPhone: 305-985-7370Website: https://visitfloridakeys.com/plan-your-trip/plan-book/events/burgers-buffet-tunes-a-tribute-show-at-comedy-key-west

  • Key West Farmers Market at Truman Waterfront

    Recurring market date listed on Marketspread schedule for the Truman Waterfront market. Date(s): May 28, 2026Venue: Key West Artisan MarketCategory: Market / ArtisanPhone: 305-731-3385Website: https://keysartisanmarket.com/farmersmarket.htm

  • Follow The Rabbit (9 PM)

    Date(s): May 29, 2026Venue: Key West TheaterCategory: MusicPhone: 305-985-0433Website: https://thekeywesttheater.com/e/?event=1365444

  • Follow The Rabbit (6 PM)

    Date(s): May 29, 2026Venue: Key West TheaterCategory: MusicPhone: 305-985-0433Website: https://thekeywesttheater.com/e/?event=1365441

  • Key West Pride Follies

    Date(s): May 30, 2026Venue: Key West TheaterCategory: Theater / LGBTQ+Phone: 305-985-0433Website: https://thekeywesttheater.com/e/?event=1367967

  • Key West Pride

    Date(s): Jun 3–7, 2026Venue: Key West Business GuildCategory: Festival / LGBTQ+Phone: 800-535-7797Website: https://gaykeywestfl.com/pride/

  • Key West Farmers Market at Truman Waterfront

    Recurring market date listed on Marketspread schedule for the Truman Waterfront market. Date(s): Jun 4, 2026Venue: Key West Artisan MarketCategory: Market / ArtisanPhone: 305-731-3385Website: https://keysartisanmarket.com/farmersmarket.htm

  • Mango Madness Opening

    Date(s): Jun 4, 2026Venue: The Studios of Key WestCategory: Arts / ExhibitPhone: 305-296-0458Website: https://tskw.org/mango-madness/

  • Burgers & Buffet Tunes

    Weekly Thursday tribute lunch show. Date(s): Jun 4, 2026Venue: Comedy Key WestCategory: Music / Lunch ShowPhone: 305-985-7370Website: https://visitfloridakeys.com/plan-your-trip/plan-book/events/burgers-buffet-tunes-a-tribute-show-at-comedy-key-west

  • Bertha: Grateful Drag

    Date(s): Jun 5, 2026Venue: Key West TheaterCategory: Music / LGBTQ+Phone: 305-985-0433Website: https://thekeywesttheater.com/e/?event=1308373

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