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8 Things to do in October 2024 in Key West

a close up of a book

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. Rocky Horror Picture Show

A red Rocky Horror Show movie banner

Key West’s Waterfront Theater presents the cult classic Rocky Horror Picture Show! Opening Oct 18 and playing 10 shows only, you can’t miss this wacky production!

Tickets sold here

2. Run a Halloween Marathon

Marathon runner running in a 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 Super-villain 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. October 24th, 6pm.


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

A gif of a bartender making fire.

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 6-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! $79 gets you everything and tips the bartenders, too!

4. Be Serenaded by a Drag Queen

A caricature of a witch.

Costumes & Drag Queens? A random Sunday is an excuse for a beautiful queen to go all out – can you imagine what Halloween is like? $50 tickets includes bottomless mimosas, specialty shots, a signature à La carte Brunch menu, and of course the ultimate Drag Queen Performances with a Live DJ!  Tickets will go fast, so Reserve Your Spot here. 


5. Key West Headdress Ball

Key West Headress Ball 2023 banner.

Join us for one of the main attractions of Fantasy Fest, the 40th Annual Key West Headdress Ball! The premier LGBTQ+ event of the Fantasy Fest Celebration, presented on Thursday, October TBA 2024, at the Coffee Butler Amphitheater, Truman Waterfront Park. Up to 15 contestants will go all out in their incredible creations to compete for the grand prize of $3000. Tickets and information link coming soon!

6. Get Your Freak On at Fantasy Fest

People enjoying a festival.

Photo // Nick Doll

While the 10-day festival will look different this year due to the word-that-shall-not-be-named, there are still many, many 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! 


7. Pedal til you DIE! Zombie Bike Ride

Zombies riding bicycles.

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 TBA, as “Zombieland” opens at Fort East Martello Museum, a reputedly haunted historic site overlooking the Atlantic Ocean at 3501 S. Roosevelt Blvd.

8.Stroll Streets with Good Eats!

Bahamian heritage dancers.

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.



Halloween banner 2024.