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

Calendar of Events for October, 2017


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Key West / April 07 to November 30
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

Key West / October 01 to October 15
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

Key West / October 08
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

Islamorada / October 08 to October 11
Islamorada Fall All-Tackle Bonefish & Permit Championship
Known locally as the "Fall All-Tackle," the three-day fishing challenge attracts energized newcomers to face seasoned veterans, in a competitive format since 1970. Up to 25 participants can fish in the tournament. One angler per boat pairs with a licensed captain to vie for division winners' trophies. The three largest bonefish and three largest permit are to be scored by length, not weight.
Contact: Betsy Bullard 305-587-1460

Key West / October 13 to October 15
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

Key West / October 13
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.

Islamorada / October 13
Friday the 13th Movies at Museum
Join the History of Diving Museum for a day of movies and monsters, and watch three films filled with aquatic thrills! Showtimes 11 a.m., 1 p.m. and 3 p.m., free admission.
Contact: 305-664-9737

Islamorada / October 15
20th Annual Keys Kids Fishing Derby
There is no charge to enter but anglers must be Monroe County residents. There are three fishing divisions: Shoreline, Backcountry and Offshore and awards for three age divisions, 4 and under, 5-7 and 8-10. There are lots of prizes with winners in all divisions! Sign up early as the first 100 registered anglers are guaranteed ditty bags. Sign up at Tackle Center of Islamorada, Caribee Boat Sales, at the Lorelei in person or online. . Lines are in at 9AM and weigh in closes promptly at 1PM.
Contact: Dianne Harbaugh 305-522-4868

Key West / October 16 to October 29
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

Key Largo / October 18 to October 22
Fifth Annual Humphrey Bogart Film Festival
The Humphrey Bogart Film Festival is to screen a rotating selection of Bogie classics and a group of movies celebrating the life and films of the man the American Film Institute named "America's greatest male screen legend." The festival, hosted by the screen legend's son, Stephen Bogart, is the only event of its kind, and is backed by the Bogart Estate. The 2017 theme is scheduled to celebrate the 75th anniversary of 'Casablanca.'

Islamorada / October 18
Immerse Yourself! Free Lecture Series at History of Diving Museum
Each month's third Wednesday features this free-admission presentation series, starting at 7 p.m. Museum exhibits are open late (entry fee applies). This month's topic of "Florida Public Archeology Network" is presented by Mallory Fenn.
Contact: 305-664-9737

Key West / October 19 to October 23
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.

Islamorada / October 20 to October 22
Ladies Let’s Go Fishing!” Keys University
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

Key West / October 20 to October 27
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.

Key West / October 20 to October 29
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

Key West / October 20 to October 21
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.

Marathon / October 21
Seventh Annual Stone Crab Claw Eating Contest
The much-anticipated opening of Florida's stone crab season takes place Oct. 15 each year, and the season opening is followed by this tasty test of crab-consuming capacity. How fast can you crack and cleanly consume 25 stone crab claws? Test your munching mettle at this zany contest. Individuals must be at least 18 years old to enter.
Contact: 305-743-4353

Key West / October 22
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 24
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

Key West / October 24
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

Key West / October 25
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 26
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.

Key West / October 26
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.

Key West / October 26
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.

Islamorada / October 26
Haunted History: Robert the Doll Returns to Islamorada
For lectures, doors open at 5 p.m., with lecture starting at 6 p.m. Cost is $25 for non-museum members, which includes museum admission, light appetizers and cash bar. Free for museum members. All lectures are at Keys History & Discovery Center, 82100 Overseas Highway, MM 82 in Islamorada, on the property of the Islander Resort, a Guy Harvey Outpost.
Contact: Reserve 305-922-2237

Key West / October 27 to October 29
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.

Key West / October 27
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.

the Florida Keys / October 28
The Florida Keys Hurricane Cup
To replace this year's normally scheduled October Backcountry Fly Series, this Keyswide backcountry fishing tournament involves scoring in 3 different locations throughout the Keys. Anglers can fish from any marina in the Keys. $500 entry fee per team. A team can consist of a guide and angler, 2 anglers, 2 guides. It is a team event. Use either Spin or Fly, both people in boat can fish. Awards include Team Grand Champions, Fly Division Champion, Spin Division Champion, Ladies Champion, Most Bonefish, Redfish, Snook, Tarpon and Permit awards. Every dollar raised is to help the Guides Trust Foundation, an organization that assists fishing guides who can't work because of serious injury or illness, and in this case, in losses suffered post-hurricane Irma.
Contact: Email: Paul Tejera

Islamorada / October 28
Mermaid Party
Come out and support local nonprofit, Coral Restoration Foundation, by dressing as your favorite sea creature and enjoying your favorite brew. All proceeds from the 4-8 p.m. event will benefit CRF and go toward restoring the Florida Keys Reef Tract. Hosted by the Florida Keys Brewing Co., at 200 Morada Way, there will be prizes for the best mermaid, merman, or sea creature costume! Raffle tickets will be available: 3 tickets for $5. At 7:00 pm, Coral Restoration Foundation will give a brief presentation on the impact of large-scale coral restoration, how you can make a difference for our oceans in your daily life, and how to get involved.

Key West / October 28
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.

Big Pine & the Lower Keys / October 30 to October 31
Southernmost Coconut Castaways' Pit Stop Party & Irma Relief FUNdraiser!
Enjoy over 40 trop rock artists over two days! From 11 a.m. to 10 p.m., headquartered at the Keys' largest tiki bar, Boondock's Grille and Draft House, MM 27.5. A newly released KEYS STRONG double CD set is to be available with 35 songs, and 100% of proceeds is to benefit United Way of Monroe County to directly support Keys residents recovering from hurricane Irma. Event admission is FREE and open to the public.