The first time we visited Key West in October, we were excited to celebrate… Halloween. Little did we know that’s not the event to celebrate in Key West, because October is all about Fantasy Fest. Well, and other things too. What are the best things to do in Key West in October?

Key West Weather

Of course, we have to talk about the weather. Everyone hopes their Key West vacation is filled with sunny and warm days, right? Well, we know that isn’t always the case. October’s average high temperature is in the low to mid 80’s. Humidity, well you know that’s still going to be a factor.

At night, expect temperatures to drop to the upper 70’s. It’s still very nice weather. October can be rainy. About 12 days this month will see rain with the average rainfall over 5 inches. But don’t fret, there are lots of things to do on rainy days in Key West, during this rainy season.

Don’t worry about the water temperature either. You can spend time on and in the water for sure!

The best water activities in Key West

October is still considered hurricane season, so, I would recommend flexibility with your plans. We just never know if a hurricane or tropical storm may make an appearance.

Plans, Planes, and Places to Stay

If you love the weird and funky side of Key West, October is the best time to visit. The first part of the month will be slow, but towards the end of the month … well hold on! It’s Fantasy Fest time. During the festivities, there are parades, street fairs, and so much fun. Don’t forget to check out all of the live entertainment along Duval Street.

Want to avoid a lot of the crowds? Go snorkeling around the coral reef, or head out on a sunset cruise.

Or plan to check out the Dry Tortugas National Park. But, book early, probably before you leave, to make sure you get a spot. This sells out very quickly!

What Not to Miss While in Key West

Planning to fly into Key West International Airport? No need to rent a car, you can walk or take the Duval Loop around the island.

Driving down the Keys? Plan to enjoy the drive, take a few days. Stay in Key Largo, Islamorada, or even Marathon.

Ultimate Road Trip from Miami to Key West

Hotel rooms, well honestly, they will be priced by demand. The period during Fantasy Fest can be pricy. So be aware. But, early in the month, still ok pricing and it’s a great time to explore the island. Much like the summer months, it can be considered “off-season”. Peak season usually is around the holidays and the winter months, because it’s a wonderful time to escape to the warm and the sun from the cold north.

Activities During October

Comedy Key West: Jon Rudnitsky – October 2 -5, 2024

Jon Rudnitsky is an actor, writer and comedian with numerous major TV and film credits including “Curb Your Enthusiasm,” “Catch-22” and “Home Again.” He was added as the only new cast member of the 41st season of “Saturday Night Live.” Shows at 8:30 p.m. 218 Whitehead St. 1

Studios of Key West: First Thursday – October 3

Celebrate the opening of October Exhibitions at the monthly First Thursday evening event from 6 to 8 p.m. when the lights stay on late, drinks are flowing and the newest gallery exhibitions come to life. Explore stunning artwork, tour artist studios, browse at Books & Books and relax on the rooftop terrace. October exhibitions include Cosmic Colors & Costumes by Guy Hermelin, The Flow of Time by Masumi Sakagami, the 40 Years of Sunsets photography exhibition, and view creative bookmark designs entered in the Summer Art Contest at Book & Books. 533 Eaton St.

Studios of Key West: 40 Years of Sunsets – Mallory Square Artists – October 3 – 31, 2024

“40 Years of Sunsets” commemorates the 40th anniversary of the iconic Sunset Celebration at Mallory Square, a cornerstone of Key West culture. This exhibition honors the tradition of celebrating the setting sun, a practice dating back to the 1830s, which has evolved into a nightly festivity uniting people from all walks of life. It features a diverse array of handmade artwork, including wire and wooden sculptures, paintings, handcrafted jewelry, fiber art, and comic books. A video presentation showcases busker and musician performances alongside interviews with participants, highlighting the celebration’s significance. 533 Eaton St.

Key West International Dance Co.: Gate 54B – October 3 – 5, 2024

See the World Premiere of Gate 54B, an Argentine tango spectacle with a twist, set at Newark Airport. A storm rages outside, planes are grounded, and the terminal is packed with stranded travelers. Amidst this chaos, a dance floor emerges. Shows at 8 p.m. at San Carlos Institute, 516 Duval St.

Marathon Community Theater: One Weekend Only – October 4 – 5, 2024

Annual silent auction and variety show fundraiser for the theater and its programs. On both nights, a silent auction filled with fantastic items and gift certificates from throughout the Keys begins at 7 p.m., with showtime at 8 p.m. The show features actors, singers and dancers from Marathon Community Theater and the community. Buffet and champagne toast to follow after the show (included with ticket). Doors open at 7 p.m.; showtimes at 8 p.m. 5101 Overseas Hwy.

ReMARCable Tour de Keys – October 5

The ReMARCable Tour de Keys is a one-day century ride (100 miles) by bicycle from Key Largo to Key West. Participants can opt for the half century ride (50 miles) from Marathon to Key West. The ride ends of Opal Key Resort in Key West. The ride raises money to support MARC, the Monroe County Association for ReMARCable Citizens, providing services for intellectually disable adults.

Fringe Theater: Zombie Prom – October 9 -13, 2024

Bravo Theatre’s Zombie Prom is like Grease Meets the Walking Dead. This musical farce is riddled with teenage heartbreak, overbearing educators, sleuthy sleuths, and Zombies, of course. The show features some of the finest young actors in Key West and is a music treat for your senses. Shows at 7 p.m. at the Armory, 600 White St.

Key West Outdoor Movies – Inside Out 2 – October 11

Key West Outdoor Movies begins its new season of free movie showings Friday, Oct. 11 with Inside Out 2, showing at the parade grounds at Fort East Martello, 3501 S. Roosevelt Blvd. The grounds open at 5 p.m. Food and drink will be available for sale by vendors onsite, and there will be free popcorn and activities for all. Bring low chairs or a blanket. The movie starts at dusk, 7:30 p.m.

Lower Keys Rotary Haunted House – Creepy Carnival – October 11

The Lower Keys Rotary’s annual haunted house returns with spine-tingling thrills to Big Pine Community Park, 31009 Atlantis Dr. As the sun sets, prepare to enter a world of frights in the Creepy Carnival. Find twisted clowns and sinister surprises lurking around every corner, ready to turn your nightmares into reality. Don’t miss out on one of the most terrifying nights of the season. The fun (and fear) begins at sunset!

Hog Heaven: Girls Night Out – The Show – October 11

Bring your friends for a night of fun with the “Girls Night Out” all-male Most Wanted Tour show at Hog Heaven, MM85.3 oceanside from 9 to 11:30 p.m. It’s going to be the most exciting ladies night out of the year. Tickets $14.95 on Eventbrite.

Florida Keys Brewing Company: Oktoberfest – October 12

Enjoy two days of Oktoberfest fun Saturday 6 to 10 p.m. and Sunday 2 to 6 p.m. in the beer garden at 81611 Old Hwy. Enjoy the live oompah band, German beer along with locally-brewed German-style beer available in one liter steins, traditional German food from Moveable Feast, a Das Boot competition, face painting and more. The celebrations are family and pet-friendly.

Southernmost Half Marathon – October 13

Runners converge on the southernmost city for their choice of a half marathon (13.1 miles) or 10k (6.2 miles). Races begin and end at Higgs Beach, 1000 Atlantic Blvd. in Key West.

Sheriff’s Animal Farm Open House – October 13

Visit the family-friendly Monroe County Sheriff’s Animal Farm, open the second and fourth Sundays of each month from 1 to 3 p.m. Visits are free of charge, but donations are always welcomed. Stock Island Detention Center, 5501 College Rd.

Waterfront Playhouse: The Rocky Horror Show – October 15 -25, 2024

This wacky musical comedy draws standing-room-only audiences at the Waterfront Playhouse each year. Book your tickets and don’t miss this irresistible show that takes place during Fantasy Fest. Showtimes at 8 p.m. Located at 407 Wall Street in historic Mallory Square.

Key West Theater: Star Wars Strips – October 17 – 24, 2024

Key West Burlesque presents “Star Wars Strips: A Burlesque Parody,” a night of light sabers and laughs that puts a cheeky twist on your favorite Star Wars characters. For ages 21 and over. Show at 8 p.m. 512 Eaton St.

Walk on White Third Thursday Art Walk – October 17

Prepare to be WOWed by the new season of Third Thursday Walk on White art walks kicking off Oct. 17 from 6 to 9 p.m. Explore an array of arts-focused offerings at more than 20 locations showcasing the works of painters, photographers, sculptors, ceramic and mixed media artists, and artisan jewelry makers while enjoying beautiful island architecture, exhibit openings, creative demonstrations, musical, literary and performance offerings and complimentary libations. In the spirit of community, each month WOW will spotlight a local non-profit organization while providing fun and creative fundraising opportunities for them. White Street between Southard and United Streets.

Key West Art & Historical Society: Happy Hour with the Historian – Building the Over-Sea Railroad – October 17

Join historian Cori Convertito for a happy hour conversation at Comedy Key West, 218 Whitehead Street, from 5 to 6 p.m. The topic is “The Eighth Wonder of the World – Building the Over-Sea Railroad.” At the time, they said it couldn’t be done and called it “Flagler’s Folly,” but it is one of the largest engineering feats the world has ever seen. The talk features a detailed look into the project, focusing on the grueling task of construction and the jubilation at its completion. Purchase tickets online in advance to secure your seat.

Studios of Key West: Smugglers’ Tales – A Reincarnation of Anne Bonny, Mary Read and Grace O’Malley – October 17

La Cucaracha Chronicles presents a new installment of the popular Smugglers’ Tales series, this time featuring the stories of female smugglers. Tony Yaniz moderates a freeform conversation between three female smugglers and a law enforcement official. As with previous Tales, their stories are completely uncensored – what’s told in the theater doesn’t leave the theater! 533 Eaton St.

Morada Way Third Thursday Art Walk – October 17

The Morada Way Arts & Cultural District’s Third Thursday Art Walk in Islamorada is the organization’s landmark, monthly event. On the Third Thursday of each month, Keys-inspired fine artists, vendors, residents, and visitors congregate on Morada Way in Islamorada to celebrate the arts and culture in the Florida Keys. Enjoy a relaxing evening from 6-9 p.m. perusing local fine art, imbibing local craft beer and wine and listening to music, in the area between mile markers 81 and 82.

Key West Art & Historical Society: Happy Hour with the Historian – Building the Over-Sea Railroad. – October 17

Join historian Cori Convertito for a happy hour conversation at Comedy Key West, 218 Whitehead Street, from 5 to 6 p.m. The topic is “The Eighth Wonder of the World – Building the Over-Sea Railroad.” At the time, they said it couldn’t be done and called it “Flagler’s Folly,” but it is one of the largest engineering feats the world has ever seen. The talk features a detailed look into the project, focusing on the grueling task of construction and the jubilation at its completion. Purchase tickets online in advance to secure your seat.

Key West International Dance Co.: Bum Farto the Musical – October 17 – 26, 2024

Building on its sold-out 2022 Key West run, KWIDC presents Bum Farto The Musical, a hilarious romp through the island’s colorful history, celebrating its quirky charm through high-energy dance numbers and unforgettable tunes. Shows at 8 p.m. at San Carlos Institute, 516 Duval St. Note: there is no show on Oct. 20.

Fantasy Fest: Barbie’s Pink Pool Party – October 18

Wear your Best Barbie or Ken pink costumes and join The Marker Key West Harbor Resort with DJ El Grace for a fun pool party for a great cause — Breast Cancer Awareness. Along with great music, there will be a Barbie or Ken costume contest, Barbie pink pools, Barbie pink drink specials, pink food specials and more, all to benefit Womankind Key West. $20 donation. 4 to 7 p.m., 200 William Street.

Fantasy Fest: Goombay Festival – October 18 -19, 2024

This exuberant street party is the official kick-off for the annual Fantasy Fest costuming extravaganza with the action taking place noon to midnight both days. Find the main entertainment stage in Key West’s Bahama Village neighborhood at the corner of Petronia and Fort streets. Popular musicians offer nonstop tunes in genres ranging from gospel to calypso and vendors offer multicultural taste treats. Other festival highlights include Friday night’s Junkanoo Rush and Saturday night’s traditional Junkanoo parade of costumed marchers and dancers, beginning at 6 p.m. and traveling through Key West’s historic downtown.  

Crane Point Museum: Witches in the Hammock – October 18 – 19, 2024

Tis the season to walk with witches through Crane Point Hammock! Open Friday and Saturday nights, Oct 18-19 from 6:30 to 9 p.m. Take a torch walk on the nature trails to someplace haunted. Watch the witches dance, visit with Casper the Friendly Ghost, enjoy the kids costume contest and hayrides, and find food including hot dogs, chili dogs, corn dogs and roasted corn. Adult beverages for purchase. Adults $15; kids $5. 5550 Overseas Hwy.

Key West Fantasy Fest – October 18 – 27, 2024

“It’s a 90s Neon Cosmic Carnival” is the official theme for Fantasy Fest 2024, Key West’s annual multi-day costuming extravaganza in paradise. From October 18-27, revelers can explore an array of exciting events, including the the exuberant Goombay Festival in the streets, the Zombie Bike Ride, a 90s-neon-themed 5K run/walk, the Captain Morgan Masquerade March (aka “Locals Parade”), the Royal Coronation of the 2024 Fantasy Fest King and Queen, plus concerts, theater productions, the enchanting Key West Pet Masquerade, the 41st annual Headdress Ball pageant, and the world-famous Key West Fantasy Fest Parade on Saturday, Oct. 26.

Key Largo Witches Ride – October 19

Witches and warlocks, too are invited to join in for the annual Witches Ride fundraiser starting at noon at The Catch Restaurant & Bar, MM 102, for a welcome party. Wear your witchiest outfits for the costume and decorated bike contest. Then, witches take flight, traveling by bike, golf cart, car or broom to the Caribbean Club, MM 104, for a big backyard bash starting at 2 p.m. with spooky specialty cocktails and live music. Raffles and a silent auction benefit the Joey Patterson Memorial Scholarship Fund and local families in need.

Underwater Pumpkin Carving Contest – October 19

Amoray Dive Resort presents the 26th annual Underwater Pumpkin Carving Contest. Divers are provided with cleaned pumpkins, then must carve out a creative jack-o-lantern while submerged in the ocean off Key Largo. The theme for this year’s contest is “Creatures From the Black Lagoon.” Carvers of the top 3 pumpkins, chosen by the Amoray dive captain and mate, are to receive prizes. Check in 12:30 p.m. Boat departs at 1 p.m. The contest is for divers, but snorkelers may go along on the trip. Mile marker 104.5.

Tribute to the Buena Vista Social Club Featuring Cortadito – October 19

Enjoy this live musical tribute to the Buena Vista Social Club and their distinctive brand of Cuban Country by the group Cortadito from Miami. The evening of live music begins at 6 p.m. in the beer garden at Florida Keys Brewing Company, 81611 Old Highway. Community Arts & Culture presents the evening, free of charge, in celebration of Hispanic Heritage Month and “La Hispanidad,” the shared culture and identity among people who speak Spanish.

Islamorada Brewery & Distillery: Alien Invasion Halloween Party – October 19

Prepare for a night that’s out of this world at a cosmic celebration featuring a costume contest where the best alien outfits will win stellar prizes. Sip on specialty shots and galaxy-inspired drinks and dance to futuristic beats and Halloween hits on the space-themed dance floor. The futuristic fun starts at 7 p.m. and goes to 11 p.m. MM 82.2 oceanside.

Fantasy Fest: Zombie Bike Ride – October 20

The annual Rock n’ Roll costumed Zombie bike ride returns for another wild run on Sunday, Oct. 20. The Zombieland pre-ride party takes place at Fort East Martello, 3501 S. Roosevelt, from 2 to 6 p.m. with face and body painters, food vendors and a full bar. The ride, with thousands of costumed zombies, rolls out at 6 p.m. going down A-1-A then through downtown. The ride ends with a dance party at the Coffee Butler Amphitheater at Truman Waterfront Park presented by Rams Head. Register online in advance for $10.

Key West Artisan Market: Fantasy Fest Zombie Watch Party – October 20

If you’re more of a watcher than a rider during the annual Zombie Bike Ride, the Key West Artisan Market keeps the party going from 5 to 7 pm at Indigenous Park at Higgs Beach, 1801 White St., just in time for the official Zombie Ride. Bring your lawn chairs and get ready for the best seats in the house along Atlantic Blvd. Find a full bar from Great Events Catering, food trucks and vendors.

Fantasy Fest: 90s Neon 5k Run/Walk – October 21

Formerly the Heroes & Villains 5k, the costumed race on the Monday of Fantasy Fest is now the 90s Neon 5k! The race takes off from Tiki House Key West, 203 Duval St., at 6 p.m. Register for the 5k run or walk or opt for the 90s Neon Mile. All participants receive fab race swag including a race T-shirt, glow-in-the-dark finisher medal, a mid-race neon jelly shot, free neon-themed drink, signature Hostess Twinkie cakes and more, plus a post-race party at Tiki House.

Dante’s Pool Bar: Under the Sea Party to Benefit Reef Relief – October 21

The annual Under the Sea Party to benefit Reef Relief takes place Monday, Oct. 21 from 12 noon to 6 p.m. with a costume contest, raffle, prizes, a DJ spinning tunes, drink specials and more.

Fantasy Fest: Pet Masquerade – October 23

Costume yourself and your critter(s) to compete, or applaud from the audience at the annual wild and wacky Pet Masquerade at the Coffee Butler Amphitheater during Fantasy Fest. Registration fees benefit the Monroe County Sheriff’s Office Animal Farm. Registration at 5:30 p.m.; show starts at 6:30 p.m. $25 to enter; free to watch. 21 Quay Rd.

Fantasy Fest: LUV2GLOW Party – October 23

The LUV2GLOW Party is Fantasy Fest’s official and longest running glow-in-the-dark blacklight dance party, and it is back for its 12th glowing year. “SPACE RAVE” is the theme — a nod to the main Fantasy Fest theme, 90s Neon Cosmic Carnival. Plan your galactic UV blacklight reactive costumes and body paint with a sexy glowing space twist. Think aliens, 90s rave gear, planets, stars, astronauts or however your mind translates SPACE RAVE. Remember NO GLOW, NO ENTRY. 8 p.m. to 2 a.m., Rick’s Upstairs, 200 Duval St. Get tickets at EventBrite.

Fantasy Fest: Key West Headdress Ball – October 24

Talented headdress makers compete for first- through third-place prizes. The premiere LGBTQ event of the Fantasy Fest Celebration, this popular event returns to the Coffee Butler Amphitheater in Truman Waterfront Park. Doors open to the outdoor gala at 6:30 p.m., show starts 8 p.m. Sponsored by the Key West Business Guild. Tickets include VIP tables, reserved chair seating and lawn tickets. 21 Quay Rd.

The Key Players: The Addams Family Musical – October 24 – 27, 2024

This musical is a comical feast that embraces the wackiness in every family. Wednesday Addams, the ultimate princess of darkness, has grown up and fallen in love with a sweet, smart young man from a respectable family– a man her parents have never met. And if that wasn’t upsetting enough, Wednesday confides in her father and begs him not to tell her mother. Now, Gomez Addams must do something he’s never done before– keep a secret from his beloved wife, Morticia. Everything will change for the whole family on the fateful night they host a dinner for Wednesday’s “normal” boyfriend and his parents. Shows at 7:30 p.m. at Coral Shores High School Performing Arts Center, MM 89.9 oceanside.

Fantasy Fest: Fantasy Market – October 25

Shop for costumes, accessories, T-shirts and other Fantasy Fest swag along with local art and great food and beverages from 10 a.m. to 4 p.m. at the Fantasy Market, located this year just 2 blocks off Duval St. at the open area in front of Conch Republic Seafood Company on Greene St. in the Historic Seaport. Enter for a chance to win 2 tickets to the VIP Parade Suite at the LaConcha hotel during Saturday night’s Bud Light Fantasy Fest Parade.

Fantasy Fest: Masquerade March – October 25

Fantasy Fest: Key West Fantasy Fest Parade – October 26

The Key West Fantasy Fest Parade winds through the world-famous Duval Street from the Gulf of Mexico to the Atlantic Ocean. The parade is a splendid moving party with festive floats, wild walking groups, bicycle brigades and human-powered kinetic machines that entertain tens of thousands spectators in the premier Fantasy Fest event. This year’s parade Grand Marshals are paranormal specialist David T. Sloan and Robert the Doll, the eerie, 100+ year-old doll with a long and storied history of supernatural behaviors.

Sheriff’s Animal Farm Open House – October 27

Visit the family-friendly Monroe County Sheriff’s Animal Farm, open the second and fourth Sundays of each month from 1 to 3 p.m. Visits are free of charge, but donations are always welcomed. Stock Island Detention Center, 5501 College Rd.

Key West Theater: Yachtley Crew – October 29

Yachtley Crew is the seven-piece SoCal band that burst onto the club scene in 2017, selling out countless local venues before igniting a nationwide Yacht Rock craze. Their success caught the attention of the legendary Jimmy Buffett, who signed them to his own Mailboat Records label. The nautically suited and captain’s-hat-clad Yachtley Crew is a seven-member band in their third year of residency at the Palms Casino Resort in Las Vegas. Yacht Rock encapsulates the revival of soft rock and Top 40 hits from the late ’70s to the early ’80s, which has become a nationwide phenomenon, inspiring fans to dress the part and sing along.

Key West International Dance Co.: Dark Night of the Soul – October 30 – 31, 2024

Just in time for Halloween, Dark Night of the Soul, a dark bewitching rock ballet is a Renaissance-era exploration of mysticism and spirituality inspired by the works of Spanish mystics, with stunning music by Dan Krysa. Shows at 8 p.m. at San Carlos Institute, 516 Duval St.

50th Annual Green Parrot Halloween Party – October 31

It’ll be spooktacular Halloween night at the Green Parrot with the annual costume party and the incredible Empire Strikes Brass band with three 90-minute sets at 5:30, 10 and midnight. No cover. 601 Whitehead St.

Key West Art & Historical Society: The Antic Humor of Richard Weatherwax – Until November 24, 2024

Richard Watherwax has more than 40 years’ experience in commercial, editorial, advertising and wedding photography. After 25 years shooting in Manhattan for top corporate brand clients, Watherwax found his home in Key West where he took to the easy, laid-back atmosphere of Key West like a duck to water. He developed his own unique style of art that many have called ‘Watherwax Whimsy.’ The exhibition marks the photographer’s 90th birthday later this year. The exhibition, on display through Nov. 24, is displayed in the Bryan Gallery at the Custom House Museum, 281 Front St

Key West Tropical Forest & Botanical Garden: Scarecrows in the Garden – Until November 30, 2024

Get your spooky on at the 6th annual Scarecrows in the Forest Art exhibition and Contest. Around the corner, in a meadow or right in front of you, made from natural, recycled and repurposed material, scarecrows are found throughout the Tropical Forest & Botanical Garden. The exhibit runs Sept. 1-Nov. 30.

History of Diving Museum: Salvaging the Deep – Until December 31, 2024

Learn about some of the world’s deepest wrecks and how salvage divers got there in the museum’s featured exhibit, on display through Dec. 31. Mile marker 82.9.