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Events in Key West

Event calendar provided with the courtesy of the Monroe County Tourist Development Council.

Events in Key West for 2021

  • October 02 Key West
  • 24th Annual Key West Paddle Classic
  • Sue Cooper 305-304-4259 Email Website
  • Watersports enthusiasts on paddleboards and other self-propelled watercraft can race around the continental United States’ southernmost island during the annual Key West Paddle Classic. Presented by Lazy Dog Adventures, the 12-mile challenge takes competitors past island landmarks such as the Southernmost Point marker, Fort Zachary Taylor Historic State Park and Mallory Square, site of Key West’s nightly sunset celebration.

  • October 22 - 31, 2021 Key West
  • Key West Fantasy Fest
  • Website
  • This outrageous 10-day costuming and masking celebration features dozens of masquerade competitions, themed parties and other exuberant events. The 2021 theme is 'All a Daze for a Holiday!' Check the website for the full schedule and more details.

  • October 26 Key West
  • Key West Burlesque presents: Harry Potter and the Enchanted Tassle, A Parody
  • Website
  • Ready your wands and study your spells! It's time to enter the wizarding world of Harriet Potter and the Enchanted Tassel: A Burlesque Parody. Whether you're Gryffindor, Ravenclaw, Hufflepuff, or Slytherin, this enthralling show is sure to have you on the edge of your Nimbus 2000 as you join Auntie Harriet Potter on a salacious search for a magical missing tassel. Doors open 7PM, show starts 8PM at Key West Theater, 512 Eaton St.

  • November 07 - 14, 2021 Key West
  • Race World Offshore World Championship
  • Website
  • Racing teams and fans are to gather in Key West for an amazing Offshore World Championship experience. RWO is the premier Offshore Racing Sanctioning body in the United States and is dedicated to producing an unforgettable week. With the most experienced team in all of offshore racing around the world, RWO anticipates another spectacular event.

  • November 14 Key West
  • Montessori United 5k & Kids' Fun Run
  • Website
  • Walk, run or stroll this 5K/1m/.5m to support Montessori education in Key West! Finisher medals given to all participants, t-shirts to the first 150 to register. Award medals for the 5K and 1mile races! Starts at 8 a.m., Higgs Beach. Register online. Proceeds benefit May Sands Montessori School & the Montessori Children's School.

  • November 17 - 21, 2021 Key West
  • Key West Film Festival
  • Website
  • Showcasing films that exhibit excellence in storytelling, the festival's lineup is to feature special events, as well as screenings at Tropic Cinema, 416 Eaton St. The four-day program is to include several films from multiple genres and categories as well as social events with filmmakers, actors and film lovers. KWFF strives to showcase the best of Florida filmmaking talent, while highlighting visiting filmmakers and industry leaders through discussions and workshops, with access to some of the biggest names in the film business. The festival also looks to support the next generation of local student filmmakers with scholarships and other key awards.

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