Calendar of Events
Current Florida Keys Events
- Sponsored Event
- Oct 17, 2024 - Oct 20, 2024 Key Largo
- REEF Fest 2024
- Website Key Largo, FL
- 305-852-0030 E-mail
- Join us for REEF Fest 2024 and celebrate ocean conservation! Come together for a weekend filled with diving, snorkeling, and kayak eco-tours. Enjoy engaging seminars and connect with fellow ocean lovers!
- Call now!
- Sponsored Event
- Oct 04, 2024 - Oct 06, 2024 Key Largo
- Take Stock In Children Backcountry Challenge
- Website Florida Keys Elks Lodge
- 92600 Overseas Hwy Tavernier FL 33070
- Key Largo Rotary E-mail
- Join the 24th annual Take Stock in Children Backcountry Challenge! A weekend of catch-and-release fishing, a kickoff party and an awards banquet! Proceeds go to the Take Stock in Children program, funding scholarships for students in Monroe County.
- Buy tickets!
- Sponsored Event
- Jan 18, 2025 - Jan 19, 2025 Key West
- Key West Half Marathon & Runfest
- Website Key West Historical Seaport
- 231 Margaret Street Key West FL 33040
- 305-240-0727 E-mail
- View video
- The 27th Anniversary of the Key West Half Marathon & 5k will take place during the week-end of January 18-19, 2025. On top of previous years race day events, this years race will include the Papa’s Pilar Rum Stroll and Key West Beach N’ Beer Mile!
- Buy tickets! Call now!
- Sponsored Event
- Oct 18, 2024 - Oct 27, 2024 Key West Arts & Culture
- Fantasy Fest 2024
- Website Key West
- 305-295-9112 E-mail
- View video
- This outrageous 10-day costuming and masking celebration features flamboyant masquerade competitions, and over 30 cleverly themed Parties and performances. Togas, Tutu’s, Body Paint and Burlesque, Halo’s, and Homemade Bikinis. Join the fun!
- Buy tickets! Call now!
- Sponsored Event
- Jan 09, 2025 - Jan 12, 2025 Key West
- KEY WEST LITERARY SEMINAR
- Website Coffee Butler Amphitheater
- 21 Quay Rd Key West FL 33040
- 305-293-9291 E-mail
- View video
- Calling all readers! The 42nd annual Key West Literary Seminar explores “Family” with renowned authors like John Irving, Ayana Mathis, and S.A. Cosby. Four days of engaging talks, book signings, music, and parties celebrating this vibrant literary city!
- Buy tickets! Call now!
- Sponsored Event
- Nov 30, 2024 - Nov 30, 2024 The Lower Keys
- The Island Art Festival 2024
- Website Lower Keys Chamber Grounds MM31
- 31020 Overseas Hwy | Mile Marker 31 Big Pine Key FL 33042
- Lower Keys Chamber of Commerce E-mail
- 'Tis the season for unique finds! Discover hand-crafted treasures, stunning art, and specialty gifts perfect for every holiday wish list. With something for everyone and prices that sparkle, your holiday shopping just got a lot more fun!
- Buy tickets!
- May 17, 2024 - Dec 31, 2024 Islamorada Arts & Culture
- History of Diving Museum: Salvaging the Deep
- Website
- 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.
- Sep 1, 2024 - Nov 30, 2024 Key West Arts & Culture
- Key West Tropical Forest & Botanical Garden: Scarecrows in the Garden
- Website
- 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.
- Sep 3, 2024 - Oct 13, 2024 The Florida Keys
- Kids Keys Deals
- Website
- The Florida Keys extends an invitation to all families to enjoy the Conch Republic, September through October 2024. During the six-week long celebration kids will be treated to free admission to attractions and tours, dining deals and other perks throughout the Florida Keys island chain. With multiple offers and warm fall weather without the summer crowds or prices, big fun is in store for kids, with savings you’ll love. Visit the website to find coupons and information on offers.
- Sep 13, 2024 - Nov 24, 2024 The Florida Keys Arts & Culture
- Key West Art & Historical Society: The Antic Humor of Richard Weatherwax
- Website
- 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.
- Oct 2, 2024 - Oct 5, 2024 Key West Arts & Culture
- Comedy Key West: Jon Rudnitsky
- Website
- 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
- Oct 3, 2024 - Oct 31, 2024 Key West Arts & Culture
- Studios of Key West: 40 Years of Sunsets - Mallory Square Artists
- Website
- “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.
- Oct 3, 2024 - Oct 5, 2024 Key West Arts & Culture
- Key West International Dance Co.: Gate 54B
- Website
- 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.
- Oct 4, 2024 - Oct 6, 2024 Key Largo Fishing
- Take Stock in Children Backcountry Challenge
- Website
- This annual tournament offers anglers the opportunity to win coveted trophies for trout, snook and redfish. Fishing is allowed around the clock from Friday night through Sunday afternoon. A popular weekend auction showcase and Sunday evening dinner are open to the public. Proceeds support local vocational scholarships for all ages and Take Stock in Children scholarships for financially challenged Upper Keys students.
- Oct 4, 2024 - Oct 5, 2024 Marathon Arts & Culture
- Marathon Community Theater: One Weekend Only
- Website
- 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.
- Oct 5, 2024 The Florida Keys
- ReMARCable Tour de Keys
- Website
- 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.
- Oct 9, 2024 - Oct 13, 2024 Key West Arts & Culture
- Fringe Theater: Zombie Prom
- Website
- 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.
- Oct 11, 2024 Marathon Arts & Culture
- Marathon Community Park: Trunk or Treat
- Website
- Bring the kids in costume to Marathon Community Park Oct. 11 from 6 to 8 p.m. for Trunk or Treat. Find candy, games and lots of fun at this early-season Halloween activity. 200 36th St.
- Oct 11, 2024 Key West Arts & Culture
- Key West Outdoor Movies - Inside Out 2
- Website
- 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.
- Oct 11, 2024 - Oct 13, 2024 The Lower Keys Arts & Culture
- Lower Keys Rotary Haunted House - Creepy Carnival
- Website
- 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!
- Oct 11, 2024 Islamorada Arts & Culture
- Hog Heaven: Girls Night Out - The Show
- Website
- 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.
- Oct 12, 2024 Islamorada Arts & Culture
- Florida Keys Brewing Company: Oktoberfest
- Website
- 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.
- Oct 13, 2024 The Lower Keys
- Coastlove: Boca Chica Beach Cleanup
- Website
- Boca Chica is a favorite spot enjoyed by visitors, Keys locals and the wildlife that call it home. Join Coastlove from 9 a.m. to 12 p.m. for a morning of sun, fun and positive impact. Join the effort to make a difference and receive snacks and giveaways. Reusable bags and gloves will be provided. Be sure to bring your own reusable water bottle to refill. 354 Boca Chica Rd.
- Oct 13, 2024 Key West
- Southernmost Half Marathon
- Website
- 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.
- Oct 13, 2024 Key West
- Sheriff’s Animal Farm Open House
- Website
- 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.
- Oct 14, 2024 - Oct 16, 2024 Islamorada Fishing
- Islamorada Fall All-Tackle Bonefish and Permit Tournament
- E-mail Website
- The 54th annual challenge attracts energized newcomers to face seasoned veterans. One angler per boat pairs with a licensed captain to vie for division winners’ trophies for the three longest bonefish and three longest permit. Kickoff and registration takes place Sun. Oct. 13 at 6 p.m. at Islamorada Fishing Club, MM 80.9 oceanside. Launch from any location is permitted for fishing Monday through Wednesday, with the awards dinner at 5:30 p.m. Wednesday at the club. For information contact Wesley Locke, 941-268-1331 or wesley@lockeandkeyproductions.com
- Oct 15, 2024 - Oct 25, 2024 Key West Arts & Culture
- Waterfront Playhouse: The Rocky Horror Show
- Website
- 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.
- Oct 17, 2024 - Oct 24, 2024 Key West Arts & Culture
- Key West Theater: Star Wars Strips
- Website
- 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.
- Oct 17, 2024 - Oct 20, 2024 Key Largo Environmental
- Reef Fest 2024: An Annual Celebration of Marine Conservation
- E-mail Website
- Ocean lovers attend REEF Fest each fall to celebrate their love of marine life and learn about the latest in conservation. Hosted by the REEF Environmental Education Foundation, the schedule is to include dive, snorkel and kayak trips, seminars with renowned ocean experts, social gatherings and more.
- Oct 17, 2024 Islamorada Arts & Culture
- Morada Way Third Thursday Art Walk
- Website
- 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.
- Oct 17, 2024 Key West Arts & Culture
- Walk on White Third Thursday Art Walk
- Website
- 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.
- Oct 17, 2024 - Oct 20, 2024 Marathon Fishing
- Marathon Offshore Swordfish Tournament
- Website
- Anglers choose two out of the three tournament days to fish this daytime swordfish tournament -- Friday the 18th, Saturday the 19th and/or Sunday the 20th. First and second place cash prizes of $12 thousand and $5 thousand respectively are to be awarded for the largest swordfish with at least six boats entered. If there are fewer than six boats, there will be a 70/30 split. The first three places are to be awarded swordfish head mounts by Gray Fish Mounts.
- Oct 17, 2024 - Oct 26, 2024 Key West Arts & Culture
- Key West International Dance Co.: Bum Farto the Musical
- Website
- 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.
- Oct 17, 2024 Key West Arts & Culture
- Key West Art & Historical Society: Happy Hour with the Historian - Building the Over-Sea Railroad
- Website
- 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.
- Oct 17, 2024 Key West Arts & Culture
- Studios of Key West: Smugglers' Tales - A Reincarnation of Anne Bonny, Mary Read and Grace O'Malley
- Website
- 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.
- Oct 17, 2024 Marathon Environmental
- Curry Hammock State Park: Sun Safe Viewing
- Website
- Explore the sun's mysteries with ranger Libby Elliott. She'll guide attendees through activities to learn about our magnetic sun, including safe telescope viewing of the sun from 10 a.m. to 12 p.m. Regular park admission applies. MM 56.2 oceanside.
- Oct 18, 2024 Key West Arts & Culture
- Fantasy Fest: Barbie's Pink Pool Party
- Website
- 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.
- Oct 18, 2024 - Oct 19, 2024 Marathon Arts & Culture
- Crane Point Museum: Witches in the Hammock
- Website
- 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.
- Oct 18, 2024 - Oct 19, 2024 Islamorada Fishing
- Casting for Cats Backcountry Tournament
- Sharon Mahoney Ellenwood 305-664-2012 Website
- This formerly all-female tournament now has a co-ed division and a women’s division. Anglers earn points for catching bonefish, permit, tarpon, snook and redfish using bait, artificial lures or fly tackle. Points are also awarded for ladyfish, sharks, jacks and spotted seatrout. The event is a major fundraiser to help control the feral cat population in the Upper Keys.
- Oct 18, 2024 - Oct 19, 2024 Key West Arts & Culture
- Fantasy Fest: Goombay Festival
- Website
- 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.
- Oct 18, 2024 - Oct 20, 2024 Islamorada Fishing
- Ladies Let’s Go Fishing! Keys Saltwater Weekend Seminar & Fishing Fever Inshore/Offshore Tournament
- Betty Bauman 954-475-9068 E-mail Website
- Female fishing fans can learn or polish angling skills during the award-winning weekend seminar and Fishing Fever tournament. More than 8,000 female graduates have immersed themselves in the annual lighthearted yet skills-heavy curriculum to learn and hone abilities in offshore, bottom, inshore and fly fishing.
- Oct 18, 2024 - Oct 27, 2024 Key West Arts & Culture
- Key West Fantasy Fest
- Website
- "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.
- Oct 19, 2024 Key Largo Arts & Culture
- Key Largo Witches Ride
- Website
- 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.
- Oct 19, 2024 Key Largo Arts & Culture
- Underwater Pumpkin Carving Contest
- Website
- 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.
- Oct 19, 2024 Islamorada Arts & Culture
- Tribute to the Buena Vista Social Club Featuring Cortadito
- Website
- 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.
- Oct 19, 2024 Key Largo Arts & Culture
- A Very Pinfish Halloween Bash
- Website
- Have a frightfully fun time at Pinfish starting at 3 p.m. with a costume contest for the kiddos. Dress them up in the cutest or creepiest attire for a chance to win prizes. Then, after the sun sets and until 10 p.m., it's time for the adults-only Haunting Bash, with costume contests, bowl-offs, happy hour brews, spooky menu specials, plus the chance to challenge the staff at games for wicked prizes.
- Oct 19, 2024 Islamorada Arts & Culture
- Islamorada Brewery & Distillery: Alien Invasion Halloween Party
- Website
- 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.
- Oct 20, 2024 Key West Arts & Culture
- Key West Artisan Market: Fantasy Fest Zombie Watch Party
- Website
- 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.
- Oct 20, 2024 Key West Arts & Culture
- Fantasy Fest: Zombie Bike Ride
- Website
- 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.
- Oct 21, 2024 Key West
- Fantasy Fest: 90s Neon 5k Run/Walk
- Website
- 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.
- Oct 21, 2024 Key West Environmental
- Dante's Pool Bar: Under the Sea Party to Benefit Reef Relief
- Website
- 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.
- Oct 23, 2024 Key West Arts & Culture
- Fantasy Fest: Pet Masquerade
- Website
- 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.
- Oct 23, 2024 Key West Arts & Culture
- Fantasy Fest: LUV2GLOW Party
- Website
- 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.
- Oct 24, 2024 Key West LGBTQ
- Fantasy Fest: Key West Headdress Ball
- Website
- 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.
- Oct 24, 2024 - Oct 27, 2024 Key Largo Arts & Culture
- The Key Players: The Addams Family Musical
- Website
- 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.
- Oct 25, 2024 Key Largo Arts & Culture
- Florida Keys Wild Bird Center: Owl-O-Ween
- Website
- Don't miss this unforgettable night of tricks, treats and conservation education from 4 to 8 p.m. at the Wild Bird Sanctuary at MM 93.6 bayside. You'll enjoy games, activities and of course, lots of candy! Explore the conservation village with local non-profit organizations setting up spooky booths with their own interactive displays and activities. Come and trick or screech with us, all while supporting your local conservation non-profits including the bird center, REEF, I.CARE, Coral Restoration Foundation, Marine Lab and Crustacean Plantation.
- Oct 25, 2024 Key West Arts & Culture
- Fantasy Fest: Fantasy Market
- Website
- 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.
- Oct 25, 2024 Key West Arts & Culture
- Fantasy Fest: Masquerade March
- Website
- Join the hugely popular Fantasy Fest tradition known as the locals’ parade that highlights costumes, creativity and community. The Captain Morgan Masquerade March is a grown-up moving cocktail and dance party that begins at 5:30 p.m. at Truman Ave. and Frances St. The route winds its way north to Fleming St., stopping at participating guest houses that hand out complimentary beverages.
- Oct 26, 2024 Key West Arts & Culture
- Fantasy Fest: Key West Fantasy Fest Parade
- Website
- 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.
- Oct 26, 2024 Key Largo Arts & Culture
- John Pennekamp Coral Reef State Park: Halloween at Pennekamp
- Website
- Bring the kids to Pennekamp for an evening of spooky Halloween fun! From 5:30 to 8:30 p.m., you can take a walk through the specially decorated "A-scare-ium;" walk either the Spooky Trail with scary actors, or the Spooky Trail without scary actors; watch shows by Captain Coral; enjoy a Mermaid Meet-and-Greet; and then, gather candy at the Trunk or Treat in the Cannon Beach parking lot. Admission is free!
- Oct 27, 2024 Key West
- Sheriff’s Animal Farm Open House
- Website
- 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.
- Oct 29, 2024 Key West Arts & Culture
- Key West Theater: Yachtley Crew
- Website
- 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.
- Oct 30, 2024 - Oct 31, 2024 Key West Arts & Culture
- Key West International Dance Co.: Dark Night of the Soul
- Website
- 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.
- Oct 31, 2024 Key West Arts & Culture
- 50th Annual Green Parrot Halloween Party
- Website
- 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.