Back to Key West's Food & Travel Resource Guide

8 Things to do in October 2019 in Key West



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. Watch A Movie on the Lawn

Cooler weather brings back the blankets and lawn chairs out! The Sunset Green, between 24 North and Gates Hotel, will screen The Breakfast Club for you 80’s fanatics on October 12th at 8pm. FREE ADMISSION!


2. Let your Inner Mermaid OUT!


Let the siren’s song lead you to the Breakfast Club, Too, whose hosting an enchanted evening under the sea. See Sultry sirens donning glamorous gowns, salty captains dressing distinguished,  mind-blowing mermaids, “mervelous entertainment,” and an ocean full of unique masks that will be sure to make you feel “a part of  their world.” $30 military, $75 General admission. Tickets  available in advance or at the door


3. Win a Prize and Feast for Your Eyes!

Photo // Waterfront Playhouse

Be the next contestants on Madame DuJours Magical Game Show and Burlesque Experience! This astonishing, interactive event features world renowned magician, Nick Locapo, leading a spectacle that is one part live game show, two parts theatrical burlesque performance, and all parts fun!

Audience members compete for a chance to win actual cash and prizes as performers entertain with miraculous amusement on stage at the Waterfront Playhouse, October 19-26. Doors open at 7:30pm – Show starts at 8pm. Tickets are $55-$65 and are available 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 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 6th Annual Heroes and Villains 5K Walk/Run during Fantasy Fest. October 22, 6pm.


5. Get “Lit” on a Cocktail Crawl

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! $65 gets you everything and tips the bartenders, too!


6. 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 19-20!


7. 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.


8. Fan Girl/Boy out with Michael Franti

Photo // Vernon Morning Star

Michael Franti is widely known for his hi-energy live shows, inspiring music, and worldwide philanthropy efforts. His mission is to use music to create positive change in the world, spreading the joy of music and positivity. So come see what he’s all about! Blankets welcome. Openers include: Dustin Thomas, Victoria Canal

Tickets are $75, show starts 6 p.m. at Sunset Green Event Lawn, 3820 N. Roosevelt Blvd.