Key West Key West Key West Key West Key West

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 07 - 28, 2021 Key West
  • Smallest Parade in the Universe
  • Website
  • Everyone’s favorite miniature parade returns! Artists compete for cash prizes and bragging rights with pint-sized floats to suit this year’s Fantasy Fest theme: All-A Daze for a Holiday! The fantastical entries are on view all month before being auctioned Oct 23 at 7 p.m., at The Studios of Key West, and 533 Eaton St., with proceeds to benefit MARC House.

  • October 10 Key West
  • Justin Hayward, Nights Tour
  • Website
  • The voice of Moody Blues joins Mike Dawes for a night of music at Key West Theater, 512 Eaton St. Doors open 7 p.m.; show starts 8 p.m.

  • 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 03 Key West
  • The Studios of Key West presents: The Mon Valley Medium
  • Website
  • Alec Silberblatt’s one-person play tells the story of Mack, a yinzer (meaning he grew up and lives in the Mon Valley of Western PA) who always believed in ghosts. But after the local medium proves himself to be a fraud, Mack is left questioning what is true and what is perception. In his darkly comic tale, Silberblatt takes the audience through one man’s involvement in a vigilante killing, and into an investigation of why we believe what we believe. Held in the The Studios of Key West Courtyard at 529 Eaton St. Show starts 6:30 p.m. Tickets available online. Seating is limited.

  • 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 07 Key West
  • Mike Nash & Southern Drawl Band
  • Website
  • With story teller songs about life and love, lyrical tales from the unique people he's met along the way, and of course plenty of summertime "drinkin' at the lake tunes" with an island-inspired twist, there's something in a Mike Nash show for everyone to relate to. Doors open 6 p.m.; show starts 7 p.m. at Key West Theater, 512 Eaton St.

  • November 09 - 11, 2021 Key West
  • Bum Farto: The Musical
  • Website
  • Based on a true and crazy Key West story, this show features an exceptional cast of 18 singers, dancers and actors performing 14 song and dance numbers in styles ranging from salsa to Carolina Shag and even includes a tap dancing ‘Square Fish’!  Show starts 8 p.m. at Key West Theater, 512 Eaton St.

  • 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.

Back to the top

Advertise on our site!

© Key West Paradise. All rights reserved. Digital marketing by Two Oceans Digital. Site Map Privacy Policy ADA Compliance

Two Oceans Digital accepts no liability with regard to the accuracy of the information on this site.
Visitors to the site are advised to double check information such as dates, times, and prices.