Festival began Apr 17, 2026; included here because it overlaps the requested date range. Date(s): Apr 21–26, 2026 Venue: Conch Republic / Key West Category: Festival Phone: 305-296-0213 Website: https://conchrepublic.com/
Arts & cultural listing notes public reception on Apr 22 and sale dates through May 8. Date(s): Apr 22–May 8, 2026Venue: Key West Woman's Club / McKee FundCategory: Arts / […]
Date(s): Apr 26, 2026Venue: Waterfront PlayhouseCategory: Theater / FundraiserPhone: 305-294-5015Website: https://www.onthestage.tickets/show/waterfront-playhouse/69d5691b39888c3830cd4f63
Date(s): Apr 26, 2026Venue: Key West TheaterCategory: MusicPhone: 305-985-0433Website: https://thekeywesttheater.com/e/?event=1210693
Date(s): Apr 27, 2026Venue: Key West TheaterCategory: MusicPhone: 305-985-0433Website: https://thekeywesttheater.com/e/?event=1253418
Date(s): Apr 28–30, 2026Venue: Tennessee Williams TheatreCategory: DancePhone: 305-296-1520Website: https://visitfloridakeys.com/plan-your-trip/plan-book/events/key-west-international-dance-company-presents-long-live-lambada
Date(s): Apr 29, 2026Venue: Key West TheaterCategory: Music / FestivalPhone: 305-985-0433Website: https://thekeywesttheater.com/e/?event=1352897
Date(s): Apr 29, 2026Venue: Key West TheaterCategory: MusicPhone: 305-985-0433Website: https://thekeywesttheater.com/e/?event=1357832
Date(s): Apr 29–May 3, 2026Venue: Festival / Key WestCategory: Festival / MusicWebsite: https://www.keywestsongwritersfestival.com/
Recurring market date listed on Marketspread schedule for the Truman Waterfront market. Date(s): Apr 30, 2026Venue: Key West Artisan MarketCategory: Market / ArtisanPhone: 305-731-3385Website: https://keysartisanmarket.com/farmersmarket.htm
Weekly Thursday tribute lunch show. Date(s): Apr 30, 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
Date(s): Apr 30, 2026Venue: Key West TheaterCategory: Music / FestivalPhone: 305-985-0433Website: https://thekeywesttheater.com/e/?event=1352898
Date(s): Apr 30, 2026Venue: Key West TheaterCategory: Music / FestivalPhone: 305-985-0433Website: https://thekeywesttheater.com/e/?event=1352899
Weekly Friday comedy-history show. Date(s): May 1, 2026Venue: Comedy Key WestCategory: Comedy / HistoryPhone: 305-985-7370Website: https://visitfloridakeys.com/plan-your-trip/plan-book/events/hemingway-in-a-funny-way-at-comedy-key-west
Date(s): May 1, 2026Venue: Key West TheaterCategory: Music / FestivalPhone: 305-985-0433Website: https://thekeywesttheater.com/e/?event=1352903
Date(s): May 1, 2026Venue: Key West TheaterCategory: Music / FestivalPhone: 305-985-0433Website: https://thekeywesttheater.com/e/?event=1352904
Date(s): May 1–2, 2026Venue: Comedy Key WestCategory: ComedyPhone: 305-985-7370Website: https://visitfloridakeys.com/plan-your-trip/plan-book/events/doug-benson-at-comedy-key-west
Date(s): May 1–3, 2026Venue: Red Barn TheatreCategory: Theater / MusicalPhone: 305-296-9911Website: https://visitfloridakeys.com/plan-your-trip/plan-book/events/youre-a-good-man-charlie-brown-red-barn-theatre
Date(s): May 2, 2026Venue: Key West TheaterCategory: Music / FestivalPhone: 305-985-0433Website: https://thekeywesttheater.com/e/?event=1352914
Date(s): May 2, 2026Venue: Key West TheaterCategory: Music / FestivalPhone: 305-985-0433Website: https://thekeywesttheater.com/e/?event=1352916
Date(s): May 3, 2026Venue: Key West TheaterCategory: Music / FestivalPhone: 305-985-0433Website: https://thekeywesttheater.com/e/?event=1352919
Date(s): May 3, 2026Venue: Tennessee Williams TheatreCategory: MusicPhone: 305-296-1520Website: https://twstages.com/onenightofqueen
Weekly Thursday tribute lunch show. Date(s): May 7, 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
Recurring market date listed on Marketspread schedule for the Truman Waterfront market. Date(s): May 7, 2026Venue: Key West Artisan MarketCategory: Market / ArtisanPhone: 305-731-3385Website: https://keysartisanmarket.com/farmersmarket.htm
Date(s): May 7–8, 2026Venue: Williams HallCategory: TheaterWebsite: https://visitfloridakeys.com/plan-your-trip/plan-book/events/key-west-playwrights-festival
