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  • Fantasy Fest

    Date(s): Oct 16–25, 2026Venue: Fantasy FestCategory: Festival / CostumesPhone: 786-342-3340Website: https://fantasyfest.com/

  • Burgers & Buffet Tunes

    Weekly Thursday tribute lunch show. Date(s): Oct 22, 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): Oct 22, 2026Venue: Key West Artisan MarketCategory: Market / ArtisanPhone: 305-731-3385Website: https://keysartisanmarket.com/farmersmarket.htm

  • Hemingway in a Funny Way

    Weekly Friday comedy-history show. Date(s): Oct 23, 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

  • Garrison Keillor & Erica Rhodes

    Date(s): Oct 27, 2026Venue: Key West TheaterCategory: Comedy / Spoken WordPhone: 305-985-0433Website: https://thekeywesttheater.com/e/?event=1231478

  • Burgers & Buffet Tunes

    Weekly Thursday tribute lunch show. Date(s): Oct 29, 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): Oct 29, 2026Venue: Key West Artisan MarketCategory: Market / ArtisanPhone: 305-731-3385Website: https://keysartisanmarket.com/farmersmarket.htm

  • Buffett Through the Years

    Date(s): Oct 30, 2026Venue: Key West TheaterCategory: Music / TributePhone: 305-985-0433Website: https://thekeywesttheater.com/e/?event=1367781

  • Hemingway in a Funny Way

    Weekly Friday comedy-history show. Date(s): Oct 30, 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

  • Race World Offshore World Championship

    Date(s): Nov 1–8, 2026Venue: Race World OffshoreCategory: Powerboat RacingPhone: 305-800-7223Website: https://raceworldoffshore.com/key-west/

  • Key West Farmers Market at Truman Waterfront

    Recurring market date listed on Marketspread schedule for the Truman Waterfront market. Date(s): Nov 5, 2026Venue: Key West Artisan MarketCategory: Market / ArtisanPhone: 305-731-3385Website: https://keysartisanmarket.com/farmersmarket.htm

  • Burgers & Buffet Tunes

    Weekly Thursday tribute lunch show. Date(s): Nov 5, 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

  • Hemingway in a Funny Way

    Weekly Friday comedy-history show. Date(s): Nov 6, 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

  • The Ocean Blue

    Date(s): Nov 7, 2026Venue: Key West TheaterCategory: MusicPhone: 305-985-0433Website: https://thekeywesttheater.com/e/?event=1360920

  • Bruce Cockburn & Livingston Taylor

    Date(s): Nov 8, 2026Venue: Key West TheaterCategory: MusicPhone: 305-985-0433Website: https://thekeywesttheater.com/e/?event=1304995

  • Burgers & Buffet Tunes

    Weekly Thursday tribute lunch show. Date(s): Nov 12, 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): Nov 12, 2026Venue: Key West Artisan MarketCategory: Market / ArtisanPhone: 305-731-3385Website: https://keysartisanmarket.com/farmersmarket.htm

  • Hemingway in a Funny Way

    Weekly Friday comedy-history show. Date(s): Nov 13, 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

  • Key West Film Festival

    Date(s): Nov 18–22, 2026Venue: Key West Film FestivalCategory: Film FestivalWebsite: https://keywestff.com/

  • Burgers & Buffet Tunes

    Weekly Thursday tribute lunch show. Date(s): Nov 19, 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): Nov 19, 2026Venue: Key West Artisan MarketCategory: Market / ArtisanPhone: 305-731-3385Website: https://keysartisanmarket.com/farmersmarket.htm

  • Dusty Slay

    Date(s): Nov 20, 2026Venue: Key West TheaterCategory: ComedyPhone: 305-985-0433Website: https://thekeywesttheater.com/e/?event=1185856

  • Hemingway in a Funny Way

    Weekly Friday comedy-history show. Date(s): Nov 20, 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