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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
Year: Month:   
April 07 - Nov 30, 2017, in Key West
Key West Fishing Tournament
More than 40 species of fish are targeted during these months, with divisions for men, women, junior anglers (ages 10 to 14) and Pee Wees (under 10 years old). The Key West Fishing Tournament strongly encourages the release of game fish. All participating anglers receive certificates noting their catches and qualify for a variety of prizes.
Contact: Doris Harris 305-923-5934
Email: director@keywestfishingtournament.com
October 01 - 15, 2017, in Key West
WineDineKeyWest
An annual mouthwatering promotion that celebrates affordable pricing at participating hotels and restaurants. Fans of fine food can enjoy multicourse prix fixé meals at select Key West restaurants during the event 'cooked up' to showcase indigenous cuisine and the talents of Florida Keys chefs. Register for free to take advantage of deals.
Contact: 800-474-4319
October 08, in Key West
Visit the Family-Friendly Sheriff's Animal Farm!
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 many animals at the farm. 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 house is held the second and fourth Sundays of the month.
Contact: Farmer Jeanne Selander 305-293-7300
October 13, in Key West
South Florida Symphony presents Hurricane Irma Relief Free Benefit Concert
The SFSO String Quartet is to perform Bedrich Smetana's String Quartet No. 1 in E Minor, "From My Life," and Antonin Dvorak's "American String Quartet No. 12, Op. 96." Performance begins at 7:30 p.m. at Studios of Key West, 533 Eaton St.
Email: info@southfloridasymphony.org
October 13 - 15, 2017, in Key West
Sixth Annual Standup Paddle Invitational 2017
Join a 2-mile paddle board and beach obstacle course to support Special Olympics Florida Monroe County. This all-levels event is fun for beginners and experienced paddlers alike. Race is to be a loop style course offering a great view for our spectators. Registration fee $35. Board rentals available through Lazy Dog.
Contact: 305-923-0288
Email: ruthholland@specialolympicsmonroe.org
October 16 - 29, 2017, in Key West
Key West Art & Historical Society presents: Second Annual "A Royal Retrospective"
Staged in the first floor lobby of the Custom House Museum. It is a look back at decades of Key West Fantasy Fest revelry, royalty and altruism via memorabilia, keepsakes, photographs, and posters, co-curated by Tennessee Williams Key West Exhibit curator Dennis Beaver and Society curator Cori Convertito, Ph.D.
Contact: 305.295.6616 x112
Email: cconvertitofarrar@kwahs.org
October 19 - 23, 2017, in Key West
Key West Bear Weekend
Key West, known for its rich and diverse subtropical marine and bird life, welcomes a larger and furrier species. "Bears," "cubs" and their buddies are to prowl the island during a long weekend of activities in the popular LGBT vacation destination. A jam packed schedule of pool parties, tea dances, dance parties and amazing festivities of the gayest city in the world, the tropical paradise known as Key West! Shane Tate and Bear World Magazine have joined together with the Island House Resort.
October 20 - 27, 2017, in Key West
Key West Burlesque Season presents: Taking it Off to See The Wizard, A Burlesque Parody
Fans of the infamous ruby slippers are invited to kick off the season by following the yellow brick road to Key West's Waterfront Playhouse, 310 Wall Street, for a "there's no place like home" performance with eight evening shows. This Key West Burlesque extravaganza features a hit-list of favorite local performers, international burlesque superstars, amazing aerial acrobats and all your favorite Oz icons, including Dorothy, the Lollipop Guild and flying monkeys like you've never seen before.
October 20 - 21, 2017, in Key West
Goombay Festival
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 20 - 29, 2017, in Key West
38th Annual Key West Fantasy Fest
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. The 2017 festival theme is "Time Travel Unravels." Check website for complete schedule of events!
Contact: 305-296-1817
Email: info@fantasyfest.net
October 22, in Key West
Zombie Bike Ride
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 is to begin at 2 p.m. when "Zombieland" opens at Fort East Martello Museum, a reputedly haunted historic site overlooking the Atlantic Ocean at 3501 S. Roosevelt Blvd.
October 24, in Key West
Florida Keys Council of the Arts Culture Crawl
A moderately difficult and clever hunt. Connect with the arts CULTURE CRAWL and have an afternoon of fun and frolic. The Florida Keys Council of the Arts hosts the modern, tech-savvy crawl at 2 p.m. Costumed teams of up to four people encouraged. Event begins and registers participants at the OLDEST HOUSE, 322 Duval St., and end at the La Concha Hotel, 430 Duval St.
Contact: 305-295-4369
October 24, in Key West
Toad the Wet Sprocket at Key West Theater
While most will feel the comforting familiarity of the Billboard-charting hits, "Walk on the Ocean", "All I Want", "Something's Always Wrong", and "Fall Down", new fans will also be well familiar with their new hits such as "California Wasted" which continues to climb the charts. Show starts 8 p.m.
Contact: 305-985-0433
Email: info@keywesttheater.com
October 25, in Key West
Fantasy Fest Pet Masquerade
The eccentric competition is likely to include canine, feline and avian critters strutting their stuff on an oceanfront stage. "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.
Email: petmasquerade@hotmail.com
October 26, in Key West
35th Annual Headdress Ball
The Key West Business Guild presents this premier gay and lesbian event of the Fantasy Fest celebration, proudly opens the new Key West Amphitheater at the Truman Waterfront Park. Tom Luna returns as the outrageous EmCee, with Rude Girl rocking out our sound.  Randy Roberts opens the show and is joined by some of the best of Key West local talent throughout the contest.  Over twenty five contestants will parade their Headdress creations on the amphitheater stage to vie for the $3,000 first prize.
October 26, in Key West
Key West Art & Historical Society presents: Brick House Funk Party
The funkiest party of Fantasy Fest features live DJs, raw soul, deep funk and groovy music. Free admission, starts 6 p.m., 281 Front St., outside the Custom House.
October 26, in Key West
Third Annual Smallest Parade In The Universe
A dazzling event, the Smallest Parade in the Universe takes place at 6 p.m. at The Key West Theater. Entrants build tabletop size floats that bobble down a conveyor parade route and are later sold in auction. Benefits Monroe Association for ReMARCable Citizens, a charity supporting Monroe county intellectually challenged adults. Artists, craftsmen, model makers and creative types are encouraged to participate, making floats no larger than 18 inches! Doors open at 5 p.m. for a pre-viewing.
October 27, in Key West
Fantasy Fest Masquerade March
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 27 - 29, 2017, in Key West
Flying Carrs Circus
The Flying Carrs Circus is back with an all new show called "Back in Time"! We are time traveling throughout the 20th and 21st century using all of our circus skills to guide the way! Join us for a trip through the decades and help us find aerialists, jugglers, acrobats, JP the clown, and more as we make our way back to 2017! Let's do the time warp at 1.21 giggle-watts with The Flying Carrs Circus! Show at the Studios of Key West, 533 Eaton St.
October 28, in Key West
Bud Light Fantasy Fest Parade
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.
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