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8 Things to do in October 2020 in Key West



Please keep in mind that many of these events are reoccurring and will likely be back in business 2021!  Our tours are still running, though! Click here for our tour calendar!


October: The month of body paint in Key West. You’re likely ready for the festival of debauchery, also known as Fantasy Fest, but we’re here to break down some other fun things to do in Key West this month.


1. Candy Bars and Library cards

The Key West Library is pleased to announce their 4th Annual Haunted Garden Trick or Treat program in the Library Palm Garden on Saturday October 12th from 5-7pm. This program is free and open to kids of all ages and costumes are encouraged.  Halloween candy donations are currently being accepted at the library for this program.  For more information please contact Miss Patricia at 305-292-3595.  The library is located at 700 Fleming St.

**No kids? Then come each Wednesday night this month for a different screening of your favorite horror cult classics! 5-7pm


2. Sing-a-long to the Rocky Horror Picture Show

The musical tells the story of a newly engaged couple getting caught in a storm and coming to the home of a mad scientist, Dr Frank-N-Furter, unveiling his new creation, a sort of Frankenstein styled monster in the form of a physically perfect muscle man named Rocky, complete “with blond hair and a tan”. Tickets available online. Showtimes 7 p.m.


3. Follow the white rabbit down a hole…

Take a trip down the rabbit hole into a world of wonder and whimsy! A world where the MarchHare dances with a bare derrière and tea parties are way more tasty when the Mad Hatter is only wearing pasties. “The White Rabbit’s Wonderland” at the Key West Theater, 512 Eaton St. features a hit-list of favorite local performers, international burlesque superstars, amazing aerial acrobats, brings all your favorite Wonderland icons to life. Doors open 7:30 p.m., show starts 8 p.m., age 21 and older.


4. Run a Halloween Marathon

Photo // Mile Zero Key West

Be super, be evil, be AWESOME and get your run on! Running a half marathon in paradise can only be topped by running a half marathon in paradise in a halloween costume. If you’re coming to party in Key West this October, make yourself feel better by “bundling in a run with your fun!”  Dress up as your favorite Superhero or Supervillain and run, walk, or fly to the finish line.

The first 400 to cross the finish will receive medals, featuring the pop art design series and time award medals for over 60 categories. Trophies for best costume as well for the 7th Annual Heroes and Villains 5K Walk/Run during Fantasy Fest. October 21, 6pm.


5. Get some “boos” & “bites” around Key West

Don’t schedule all the good plans at night and leave your days empty! Fill your days, your cups, and your bellies on Key West Food Tours Cocktail Crawl. Their 5-stop crafty, Off-Duval St bar crawl includes preselected 5 drinks and delicious bites throughout the tour. No wonder it’s been getting such rave reviews! $75 gets you everything and tips the bartenders, too!


6. Pedal til you DIE!

A pre-Halloween tradition for visiting and local families and groups, the ride typically draws several thousand men, women and children — and even a few pets. Garbed in ragged costumes and frightening face and body makeup, they pedal along the island city’s Atlantic Ocean shore in a deliciously scary spectacle. The wacky event begins at 2 p.m. and lasts until 6:30 p.m. on Oct 20th, as “Zombieland” opens at Fort East Martello Museum, a reputedly haunted historic site overlooking the Atlantic Ocean at 3501 S. Roosevelt Blvd.

7. Stroll Streets with Good Eats!

Photo //

Held in Key West’s historic Bahama Village neighborhood, the lively Goombay is known for its island-style food, arts and crafts, nonstop live entertainment and dancing in the streets. Visitors can experience sights, sounds and flavors recalling Key West’s Bahamian heritage. FREE event, noon to midnight both days. October 18-19!


8. Get Your Freak On at Fantasy Fest

Moving Skeleton Float operated by paraders

Photo //

The mac daddy of all things to do this month. The 10-day festival teems with both official & un-official events ranging from the Kinky Karnival to Children’s Day. It’s a wide spectrum and there’s sure to be something for you.

*For tips on how to make your Fantasy Fest the BEST one ever, click here!