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Event calendar courtesy of — The Tourism & Development council of the Florida Keys

Calendar of Events for October, 2018


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Islamorada / March 21 to December 17
History of Diving Museum presents: Immerse Yourself Free Speaker Series
The History of Diving Museum presents the annual presentation series that spotlights a new topic the third Wednesday of each month, at 7 p.m. Exhibits and museum store stay open late (normal museum admission applies).
Contact: 305-664-9737

Islamorada / October 05 to October 07
Robert James Sales Baybone Celebrity Tournament
The second tournament in the Redbone Trilogy targets permit and bonefish to raise money for cystic fibrosis research. Past participants include legendary angler Stu Apte, former Denver Bronco and Tampa Bay Buccaneer Mark Cooper and Major League Baseball Hall of Famer Wade Boggs.
Contact: 305-664-2002

Key Largo / October 05
First Friday MM 104 Block Party
Join Key Largo's new monthly, free-admission block party along the Overseas Highway at mile marker 104 in Key Largo, presented by the Upper Keys Merchants Assoc. Held the first Friday of each month, rain or shine, from 6-10 p.m., stroll among artists, street bites, gifts, eateries and more. Park at any of the MM104 businesses and walk along the bayside bike pathway.

Key West / October 05 to October 07
SoMo Marathon & Half Marathon
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.

Islamorada / October 07 to October 10
Islamorada Fall All-Tackle Bonefish & Permit Championship
Dubbed the "Fall All-Tackle," the three-day fishing challenge attracts energized newcomers to face seasoned veterans in a competition that has taken place since 1970. One angler per boat pairs with a licensed captain to vie for division winners' trophies for the three longest bonefish and three longest permit. The field is limited to 25 participants. Festivities kick off Oct. 7 and fishing days are Oct. 8-10.
Contact: Kellie Trotta 561-346-3193

Key West / October 11 to October 29
3rd Annual A Royal Retrospective: a Look Back at the Kings & Queens of Fantasy Fest
Key West Art & Historical Society presents this annual event, in the 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 Museum curator Dennis Beaver and Society curator Cori Convertito, Ph.D. And one night only - Thursday, October 18 from 6-8 p.m. - the exhibit becomes the site for an all-candidate "Royal Retrospective" party open to the public, with a cash bar and light appetizer fare, with 100% of the $10 admission benefitting AIDS Help of Monroe County. Former Fantasy Fest Kings and Queens are encouraged to attend.

Key West / October 12
Sirens Masquerade Ball
Listen to the siren's song and follow it to the BC, Too, host of an enchanted evening under the sea. Sultry sirens in glamorous gowns, salty captains looking distinguished, 'mervelous' entertainment, mind-blowing mermaids and an ocean full of unique masks will be sure to make you feel part of the undersea world. To be held at The BC, Too. Cost: $75 in advance, $85 at the door.
Contact: Kristi Mills 305-304-1988

Marathon / October 13
Coral Country Road Festival
A full day charity event of live music is on tap for the Middle Keys. Lineup includes Zach Stone, Little Texas, The Carousers, Billy Rice, Jerrod Niemann. Gates open at 11 a.m., Marathon Community Park. Musical performances start 12 p.m. - 9 p.m. Proceeds benefit Keys nonprofits including the Florida Keys SPCA, Autism Society of the Florida Keys, Project Vet Relief, and more. Craft beers, food, wine and 50+ vendors are planned. Tickets $25 pp in advance, $35 at gate, purchase in advance at
Contact: Box Office 305-295-7676

Key Largo / October 14
Underwater Pumpkin Carving Contest
Strapped with dive knives as tools and creative ideas in their heads, crafty carvers are to descend 30 feet beneath the surface in the Florida Keys National Marine Sanctuary, tasked with transforming the naturally buoyant pumpkins into masterful sculptures with frightening facial features. The top three buddy teams that create pumpkins worthy of praise from the experienced judges can win prizes including a dive trip for two and fashionable swag. Check-in is at 8 a.m. and the boat departs at 8:30 a.m. Space is limited, so contestant divers are encouraged to sign up early for the special event.
Contact: 800-426-6729

Key West / October 19 to October 26
Key West Burlesque presents: Madame DuJour’s Magical Game Show Experience
Ladies and Gentlemen, come on down! You're the next contestants on Madame DuJour's Magical Game Show and Burlesque Experience! An astonishing, interactive event awaits as Key West Burlesque and world renowned magician, Nick Locapo, take to the stage in a production that is one part live Game Show, two parts theatrical burlesque performance, and all parts fun. Each night audience members have a chance to win prizes in the ultimate episode of miraculous amusement on stage at the Waterfront Playhouse. Doors open 7:30 p.m., show starts 8 p.m.
Contact: Tickets 305-294-5015

Key West / October 19 to October 28
39th 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.
Contact: 305-296-1817

Key West / October 19 to October 20
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.

Islamorada / October 19 to October 21
Ladies Let’s Go Fishing!” Keys Saltwater Weekend Seminar & Fishing Fever Inshore/Offshore Tournament
Female fishing fans can learn or polish angling skills during the award-winning weekend seminar. More than 8,000 female graduates have immersed themselves in the annual lighthearted yet skill-heavy curriculum to learn and hone abilities in offshore, bottom, inshore and fly fishing.
Contact: Betty Bauman 954-475-9068

Marathon / October 20
Celebrate 75 Years of Aviation at Marathon Airport!
Fly or drive to the celebration! This free-admission event from 9 a.m. to 5 p.m. is to commemorate 75 years of aviation in the heart of the Florida Keys. Discover the Aviation Museum, see historic aircraft and enjoy discovery flights. Fun for all ages.
Contact: 305-289-6060

Key West / October 21
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.

Key West / October 22
Rams Head Productions presents: Michael Franti & Spearhead
Michael Franti is a musician, humanitarian, and filmmaker who is recognized as a pioneering force in the music industry. Franti believes in using music as a vehicle for positive change and is revered for his hi-energy live shows, inspiring music, and worldwide philanthropy efforts. Giving back has always been at the heart of Franti's mission. He has dedicated his life to spreading the joy of music and positivity to millions of people. Doors open 5 p.m., show starts 6 p.m. at Sunset Green Event Lawn, 3820 N. Roosevelt Blvd.

Big Pine & the Lower Keys / October 22
The Perry Hotel presents: Ringmaster's Pool Party, a Fantasy Fest Event
Join this one-of-a-kind spectacular for only $10 per person, and leave with an unforgettable Fantasy Fest experience featuring carnival games, strongman photo ops, circus-themed food and drinks, music by local favorite Patrick & The Swayzees, and more. No charge for hotel guests.

Islamorada / October 22
Matecumbe Historical Trust presents: International Archeology Day, Taste of History Dining Event
Ryan Harke, professional archaeologist will present "The Southernmost Pre-Columbian Site" Stock Island's Connection with the Upper Florida Keys and South Florida" The Stock Island Site is large and an important archaeological site which was excavated by Irving Eyster and Robert Carr in the late 20th century. In this presentation, Ryan will discuss his ongoing dissertation research into the state collections from those excavations. His goal is to reconstruct the season(s) the site was inhabited from zoo archaeological (animal/food) remains, and thereby, determine if a year-round village was present there. In addition, he will discuss how the Stock Island peoples may relate to those of the Upper Keys and mainland Florida." Ryan's current research focuses on the Native Americans and the past environments of the Florida Keys. Dinner is $50.00 per person all inclusive of tax and gratuity. at the Islamorada Moose Lodge at 6:30 p.m.
Contact: RSVP Barbara at 305-393-0940

Islamorada / October 24
Keys History & Discovery Center presents: How Tall Tales Reshape Local History
This month's lecture series features guest speaker Brad Bertelli, Historian and Author. Lectures are held at Keys History & Discovery Center, MM 82 on the property of the Islander Resort. Doors to the Discovery Center open at 5 p.m., one hour before the presentation to allow guests to view exhibits. Light appetizers and a cash bar are available. Cost is $10. Reservations advised.
Contact: 305-922-2237

Key West / October 24
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.

Key West / October 25
36th 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.

Key West / October 26
Fantasy Fest Masquerade March
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.

Islamorada / October 26 to October 27
Fall Backcountry Fly Championship Series
Tournament anglers are to compete to catch the most inches of snook and redfish on fly in a challenge where one inch equals one point. Awards are to be given to the grand champion and runner-up, and to the anglers who catch the largest snook and redfish. The field is limited to 30 boats.
Contact: Paul Tejera

Key West / October 27
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.

Marathon / October 28
Third Annual Marathon's Fall Harvest at Crane Point Museum
From 4-8 p.m., enjoy some old fashioned harvest-time fun to bring in the fall season! Hay rides, trail mazes, face painting, crafts for kids, cheeseburgers, chili dogs, apple cider, caramel apples, baked goods & live music. Admission is $5 for adults, $3 for children, free for ages 4 and under.
Contact: 305-393-9501