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Calendar of Events for the Florida Keys

Event calendar courtesy of - The Tourism & Development Councel of the Florida Keys

Calendar of Events for October
Year:   Month:   Location:  
Review other months or locations!
April 07 to November 30,  in Key West
Key West Fishing Tournament
April 07 to November 30
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

October 16 to October 29,  in Key West
Key West Art & Historical Society presents: Second Annual "A Royal Retrospective"
October 16 to October 29
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

October 18 to October 22,  in Key Largo
Fifth Annual Humphrey Bogart Film Festival
October 18 to October 22
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.'

October 18 ,  in Islamorada
Immerse Yourself! Free Lecture Series at History of Diving Museum
October 18
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

October 20 to October 29,  in Key West
38th Annual Key West Fantasy Fest
October 20 to October 29
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

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

October 20 to October 21,  in Key West
Goombay Festival
October 20 to October 21
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 21 ,  in Marathon
Seventh Annual Stone Crab Claw Eating Contest
October 21
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

October 22 ,  in Key West
Zombie Bike Ride
October 22
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
October 24
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
October 24
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

October 25 ,  in Key West
Fantasy Fest Pet Masquerade
October 25
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.

October 26 ,  in Key West
Third Annual Smallest Parade In The Universe
October 26
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 26 ,  in Key West
Key West Art & Historical Society presents: Brick House Funk Party
October 26
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 Islamorada
Haunted History: Robert the Doll Returns to Islamorada
October 26
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

October 27 to October 29,  in Key West
Flying Carrs Circus
October 27 to October 29
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 27 ,  in Key West
Fantasy Fest Masquerade March
October 27
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 28 ,  in Florida Keys
The Florida Keys Hurricane Cup
October 28
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

October 28 ,  in Islamorada
Mermaid Party
October 28
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.

October 28 ,  in Key West
Bud Light Fantasy Fest Parade
October 28
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 30 to October 31,  in Big Pine
Southernmost Coconut Castaways' Pit Stop Party & Irma Relief FUNdraiser!
October 30 to October 31
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.

Calendar of Events for October
Year:   Month:   Location:  
Review other months or locations!

All events are subject to change. Contact the event coordinators for the most current dates and times.

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