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Events in Key West

Event calendar provided with the courtesy of the Monroe County Tourist Development Council.

Events in Key West for October

  • October 11 - 12, 2019 Key West
  • SoMo Marathon & Half Marathon
  • Email Website
  • This event is one of a kind! Imagine running through the southernmost island in the United States while enjoying a break from the ordinary. The Southernmost Marathon & Half promises just that- 26.2 or 13.1 miles of ocean and gulf views, as well as iconic Key West landmarks. A full weekend of events including a 10k and 5k are planned.
  • October 13 Key West
  • Visit the Family-Friendly Sheriff's Animal Farm
  • Farmer Jeanne Selander 305-293-7300 Website
  • Open between 1 - 3 p.m., the Sheriff's Animal Farm invites you to bring the family and visit the animals at the farm, including horses, a cow, pigs, goats, bunnies, alligators, tropical birds, a Kinkajou, Sloths, a Lemur, Kramer the Emu, a family of Patagonian Cavys, tortoises and turtles, snakes and many more. It is free of charge (donations are welcome). The farm is located just off of College Road, on Stock Island, at the Sheriff's Office Headquarters complex. The Animal Farm is open every second and fourth Sundays of the month.
  • October 18 - 19, 2019 Key West
  • Bahama Village Goombay Festival
  • Website
  • Held in Key West's historic Bahama Village neighborhood, the lively, family-friendly 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 - 27, 2019 Key West
  • 40th Annual Key West Fantasy Fest
  • Website
  • This outrageous 10-day costuming and masking celebration features flamboyant masquerade competitions including one for pets, a headdress ball, exuberant promenades, street fairs and a grand parade that stars marching groups, island-style bands and lavish floats.
  • October 19 - 25, 2019 Key West
  • Waterfront Playhouse presents: Rocky Horror Picture Show
  • Website
  • 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.
  • October 20 Key West
  • Key West Artisan Market: Zombie Pre-Party Edition
  • Website
  • Browse among culinary, textile, jewelry, wood, artists & crafters, curiosities, live music, craft beer, wine and art and food concessions. From 10 a.m. to 2 p.m., at Higgs Beach. Bring your own bags. A fantastic, family-friendly, free event.
  • October 20 Key West
  • Zombie Bike Ride
  • Website
  • 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., as "Zombieland" opens at Fort East Martello Museum, a reputedly haunted historic site overlooking the Atlantic Ocean at 3501 S. Roosevelt Blvd.
  • October 23 Key West
  • Fantasy Fest Pet Masquerade
  • Email Website
  • The eccentric competition is likely to include canine, feline and avian critters strutting their stuff onstage at the Key West Amphitheater. "Party animals" can compete for costume prizes and glory. You will see a magic carousel of frisky pets and playful owners, all delightfully disguised, stroll, dance and even skateboard across a stage in a fun frolic for fame and fortune! Think you and your furry, feathered or slithery friend have the perfect outfit? Four categories to enter, $25 each entry; benefits the Lower Keys Friends of Animals. Starts 6:30 p.m.
  • October 23 - 25, 2019 Key West
  • The White Rabbit’s Wonderland: A Burlesque Parody
  • Website
  • Take a trip down the rabbit hole into a world of wonder and whimsy! A world where the MarchHare dances with a bare derrière and tea parties are way more tasty when the Mad Hatter is only wearing pasties. “The White Rabbit’s Wonderland” at the Key West Theater, 512 Eaton St. features a hit-list of favorite local performers, international burlesque superstars, amazing aerial acrobats, brings all your favorite Wonderland icons to life. Doors open 7:30 p.m., show starts 8 p.m., age 21 and older.
  • October 23 Key West
  • Wharfstock
  • Website
  • Get all keyed up for the spell of peace, love, and music--Woodstock style, and celebrate at Schooner Wharf Bar, along the historic waterfront. Don a set of bell bottoms, love beads, headbands and enter a '60s costume contest. Everyone will be getting groovy with tie-dye, flower power and psychedelic fun, starting at 7 p.m.
  • October 24 Key West
  • 37th Annual Headdress Ball
  • Website
  • The Key West Business Guild presents this premier gay and lesbian event of the Fantasy Fest celebration, at Key West Amphitheater at the Truman Waterfront Park. Some of the best of Key West local talent highlights the contest.  Contestants parade their Headdress creations on the amphitheater stage to vie for a first-place cash prize.
  • October 25 Key West
  • Fantasy Fest Masquerade March
  • Website
  • Famed as "the locals' parade," the march typically draws high-spirited revelers wearing everything from elaborate masks and costumes to offbeat creations inspired by the festival theme. Begins at the Key West Cemetery at Frances Street entrance but revelers can join the mad march anywhere along the two routes. Start marching at 5:30 p.m.; all are welcome; free admission.
  • October 26 Key West
  • Bud Light Fantasy Fest Parade
  • Website
  • The madcap merriment of Fantasy Fest is to culminate during the Bud Light Fantasy Fest Parade through Key West's historic downtown. Tens of thousands of spectators converge to cheer the parade's elaborately costumed marching groups, dancers in bright feathered costumes and dazzling motorized floats. Join thousands of exuberant partygoers! It doesn't get any wilder than this! Parade steps off at 7 p.m.; free to spectate.
  • October 26 Key West
  • Old Island Restoration Foundation presents: Fantasy Fest Porch Party
  • Website
  • Hosted by the Old Island Restoration Foundation, an all-inclusive $225 ticket includes a full-course, sit down dinner prepared by one of our favorite restaurants, served under the lights in the private backyard garden of the Oldest House Museum in the heart of historic Old Town, steps from Duval St. Our bar will be open all night serving plenty of cocktails, beer and wine. And we’ll have lots of beads! This is an exclusive event with a very limited amount of tickets. Gate opens at 5:00pm; Dinner 5:30pm; Parade Viewing on the Porch 7:00pm
  • October 27 Key West
  • Visit the Family-Friendly Sheriff's Animal Farm
  • Farmer Jeanne Selander 305-293-7300 Website
  • Looking for a fun place to take the kids? The Sheriff's Animal Farm is open 1 - 3 p.m. Bring the family and come visit the animals at the farm, including miniature horses, a cow, pigs, goats, bunnies, alligators, tropical birds, Kinkajous, Sloths, a Lemur, Kramer the Emu, a family of Patagonian Cavys, a skunk, an opossum, tortoises and turtles, snakes and many more. It is free of charge, but donations are welcomed because that is how the farm is sustained. The farm is located just off of College Road, on Stock Island, at the Sheriff's Office Headquarters complex. Open the second and fourth Sundays of the month.
  • October 28 Key West
  • The Allman Betts Band With Special Guest Jd Simo At Sunset Green Event Lawn
  • Website
  • The sons of Gregg Allman (Devon Allman) and Dickey Betts (Duane Betts) have joined forces to form The Allman Betts Band. The show features new music, songs from their solo projects and classic Allman Brothers and Gregg Allman tunes in honor of the 50th Anniversary of The Allman Brothers Band. Sunset Green Event Lawn is a new multipurpose event space located at 24 North Hotel. Sunset Green will transform into a music venue providing food, drinks, state of the art sound and production creating the ultimate concert experience. Vacation packages are available through 24 North Hotel featuring discounted hotel rates & more. Tickets available online.
  • October 31 Key West
  • Annual Halloween Conch Train
  • Ms. Bennett 305-294-1296 or 305-517-6611 Email
  • Come One, Come All Aboard! The Christian Education Department invites the public to ride the Conch Tour Train, providing safe environment and treats, for an $8 donation pp. Presented by Cornish Memorial A.M.E. Zion Church. Boarding time 5:45 p.m. at 702 Whitehead St.
  • January 26 - Oct 08, 2019 Key West
  • Impromptu Classical Concerts presents: Trio Gaspard
  • Website
  • Trio Gaspard, whose members are from Germany, Greece and the UK, is one of the most sought-after trios of its generation. Jonian Ilias Kadesha (violin), Vashti Hunter (cello) and Nicholas Rimmer (piano) have been invited to perform regularly at major international concert halls like Wigmore Hall and the Berlin Philharmonie. They have been winners of three major international competitions since their inception in 2010. All Impromptu Classical Concerts are at 4:00 PM at St. Paul’s Episcopal Church, 401 Duval St. in Old Town.

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