Skip to primary navigation Skip to content Skip to footer
Back to Key West's Food & Travel Guide

8 Things to do in October 2021 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. Family Friendly Halloween Scavenger Hunt

text

Grab your costumes and head over to the Public Library for a family-friendly, outdoor scavenger hunt. Starts Saturday Oct 9th. Ask a Librarian at the front desk for your first clue then search the library garden for 14 clues to win a prize! The scavenger hunt will stay up for the entire month of October and is available to play during library hours! For more information call 305-292-3595 or check out their website at Keyslibraries.org

 

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. Harriet Potter and the Enchanted Tassel

 

text

Ready your wands and study your spells! It’s time to enter the wizarding world of “Harriet Potter and the Enchanted Tassel” at the Key West Theater, 512 Eaton St. featuring a hit-list of favorite local performers, international burlesque superstars and amazing aerial acrobats. Doors open 7:30 p.m., show starts 8 p.m., age 21 and older. RSVP Here.

 

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 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 25th, 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. Be Serenaded by a Drag Queen

text

Costumes & Drag Queens? A random Monday is an excuse for a beautiful queen to go all out – can you imagine what Halloween is like? $40 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. 

 

7. Get Your Freak On at Fantasy Fest

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! 

 

8. Pedal til you DIE! (UPDATE: Zombie Bike Ride Canceled in 2021)

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.

Stroll Streets with Good Eats! (UPDATE: Goombay Festival Canceled in 2021)

Photo // Allevents.in

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!

 

LIKE IT? PIN IT!

graffiti on a wall

 

Skip to toolbar