The Lodging Association of the Florida Keys and Key West

Keys Events

Florida Keys & Key West Events Information, Accommodations of the Florida Keys. Plan your Island vacation around an event or holiday.
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Events in the Florida Keys for October, 2019
Year: Month:  
October 05,  in Key Largo
Underwater Pumpkin Carving
Divers become underwater artists as they turn pumpkins into Halloween masterpieces beneath the sea in the Florida Keys National Marine Sanctuary. Prizes such as dive trips are awarded the most creative jack-o-lantern. Entry fee is $85 per certified diver for the 8 a.m. two-tank, two-location dive(s) including tanks, weights, snorkel equipment and pumpkin! Space is limited, contact Amoray Dive Resort to make reservations.
Contact: 305-451-3595
Email: [email protected]

October 06,  in Islamorada
Florida Keys Tour de Reef
Are you ready to explore the Florida Keys? The ride will feature two distances that are perfect for cyclists who want a short or long adventure in the Keys with 40 and 66 mile distances. Once you finish there will be an epic post ride festival hosted at the Florida Key's Brewing Company Tap Room.

October 11,  in Big Pine
Pop and Pour at The Perry
An evening of pouring bubbles and popping some bubbly with a new version of paint-and-sip, presented by Ocean Blues Studio. In a small class setting, learn step-by-step tips and tricks for creating a masterpiece, ready to hang in your home. Perfect for date night, girls night out, bachelorette parties, mom’s night out, birthday celebration, or just because! Limited seating is available so reserve a spot today. In true island style, paint under the palm trees outside at the Perry Hotel, with drinks available through Salty Oyster Bar. Complimentary drink ticket is included with class purchase. Starts 7 p.m., at the Perry Hotel, 7001 Shrimp Rd.
Email: [email protected]

October 11 to October 12,  in Key West
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.
Email: [email protected]

October 12,  in Marathon
Fourth Annual Fall Harvest Fun at Crane Point Hammock Museum & Nature Trail
Families of all ages are welcome to come and enjoy a petting zoo, hayrides, kids face painting, bubbles and more. From 4-8 p.m., inside Crane Point, 5550 Overseas Highway. Adult beverages and food will be available for purchase. Donation admission is $5 per adult, $3 kids, age 3 and under admitted free.

October 12,  in Big Pine
Community Clean-Up with Jose Wejebe Foundation
Hosted by Jose Wejebe Memorial Foundation, volunteer and join a great cause in Summerland Key at the First State Bank from 8 -11 a.m. No tickets needed. Meet at First State Bank, Summerland Key branch, mile marker 24.7.

October 12,  in Islamorada
Morada Bay Beach Cafe Full Moon Party
Entertainers, performers, fire dancers, Junkanoo band, two restaurants, outdoor BBQ grill, VIP lounge, two DJ’s, two dance floors, world-famous 32oz mason-Jar cocktails, and a fabulous fireworks show. A night on the beach at Morada Bay Cafe that is a locals' favorite. Entry fee applies.
Contact: 305-664-3225
Email: [email protected]

October 13,  in Islamorada
Oktoberfest in Islamorada
An all-day fun day from 11AM to 9PM at Florida Keys Brewing Co., 81611 Old Highway. Highlights include a traditional German Oompa Band 4-8pm; 10 German Style beers on draft; Reefers & Green Turtle will be serving up traditional German food; Face Painting; Otherside Axe Throwing; Das Boot Competition at 2pm and 7pm; Dirndll & Lederhosen are a must! Best dressed wins a $50 bar tab. Island Sound & Lights (AKA Wood) will be rocking the stage with traditional German music 12-3pm

October 13 to October 16,  in Islamorada
Islamorada 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. 13 and fishing days are Oct. 14-16. Event is headquartered at Islamorada Fishing Club.
Contact: Kellie Trotta 561-346-3193
Email: [email protected]

October 13,  in Key West
Visit the Family-Friendly Sheriff's Animal Farm
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.
Contact: Farmer Jeanne Selander 305-293-7300

October 16,  in Islamorada
History of Diving Museum: Immerse Yourself! Free Lecture Series
Maritime archaeologist Joshua Marano will discus his involvement in the archaeological excavation of the notorious pirate Blackbeard’s Queen Anne’s Revenge (QAR) shipwreck off the North Carolina coast. Mr. Marano will share the history of the pirate Blackbeard, the loss of his flagship, its rediscovery and current work. Exhibits and Museum Store will be open until 6:45, with last exhibit tickets being sold at 6:15.

October 17 to October 20,  in Key Largo
Join Reef Environmental Education Foundation (REEF) in a celebration of marine conservation. Morning activities include ocean adventures of kayaking, snorkeling and diving, all alongside marine life experts. Afternoons feature free seminars from renowned experts in a variety of marine topics. Evenings boast food, drinks and fun with friends old and new. All events are open to the public.
Contact: 305-852-0030
Email: [email protected]

October 17 to September 17,  in Islamorada
Morada Way Arts & Cultural District's Third Thursday Art Walk
Third Thursday ArtWalks are held every month throughout the year, offering attendees live music on three stages, performance artists and, of course, original art and hand-crafted jewelry, as well as pottery, sculptures and more! This monthly event, from 6-9 p.m., is a focal point of artistic expression, culinary and cultural awareness to the Upper Keys. Stroll through the Art District, sip some craft beers, eat local food, along a quarter-mile span of the Old Highway between the historical 1935 Hurricane Monument and the iconic Green Turtle Inn and includes the intersecting street now known as Morada Way, between MM 81 and 82.

October 17,  in Big Pine
Boats, Ballads, & Sunset: An Evening with Seth Ennis and Friends
A very special evening at Oceans Edge Resort, 5950 Peninsular Ave., with country music star Seth Ennis and his singer-songwriter friends from Nashville. Seth, whose hits include “Call Your Mama” and “Woke Up In Nashville”, will be serenading you along with several special guests right at sunset overlooking the marina. Come down, have a drink, and enjoy some country tunes by the water! This event is presented in partnership with Trosset Outdoors. All tickets must be purchased in advance, $25 pp. Proceeds from this event will support Captains For Clean Water.

October 18 to October 27,  in Key West
40th 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.

October 18 to October 19,  in Key West
Bahama Village Goombay Festival
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 to October 20,  in Islamorada
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
Email: [email protected]

October 19,  in Marathon
Coral Head Blues Fest
Kick off the 2019 Fantasy Fest weekend with this newly added music event! Music acts such as Anthony Gomes, Dana Fuchs, Shaw Davis & the Black Ties, Bill Blue Band, Ghost Town Blues Band and Paul Delariers Band are to grace the stage from 11 a.m. to 10 p.m. at Marathon Community Park's amphitheater. Tickets $14 in advance, $19 at gate. Kids age 12 and under $5. Tickets available online.

October 19 to October 25,  in Key West
Waterfront Playhouse presents: Rocky Horror Picture Show
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 19,  in Key West
Key West Tropical Forest & Botanical Garden's Native Plant Sale
The Nursery at the Key West Tropical Forest & Botanical Garden will be offering native trees, shrubs and vines for sale from 9 a.m. to noon. The Garden is located at 5210 College Road on Stock Island.
Contact: 305-296-1504

October 20,  in Key West
Key West Artisan Market: Zombie Pre-Party Edition
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,  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 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 21,  in Big Pine
The Perry Hotel Key West’s Fantasy Fest Duck, Duck, Booze Pool Party
We’re kicking off Fantasy Fest with a pool party like you’ve never seen before – complete with a pool full of rubber duckies, BSB samples, swag, and live music by Key West’s favorite DJ Buggy. Don’t miss the ducky, DJ, and BSB (Brown Sugar Bourbon) takeover at The Perry Hotel. Duck floats, bathing suits, tutus, and creativity are encouraged! This event is free and open to the public, from 12-4 p.m.

October 21,  in Islamorada
Matecumbe Historical Trust presents: 'Native Americans in the Florida Keys: Similar or Different from Mainland Cultures?'
Archaeologist Ryan Harke will discuss the hypothesis that natives lived in sedentary villages throughout the Keys prior to the arrival of Europeans. He will also speak about research at the Stock Island site, which was excavated by a notable historian, the late Irving Eyster. Free presentation; open to the public; held at Island Community Church, mile marker 82, at 6:30 p.m.

October 23,  in Key West
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 23 to October 25,  in Key West
The White Rabbit’s Wonderland: A Burlesque Parody
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,  in Islamorada
Keys History & Discovery Center Presents…Beyond the Sunshine: A Timeline of Florida’s Past
Join Rick Baker, author, lawyer and former mayor of St. Petersburg, Florida’s fourth largest city, as he shares how lessons learned from Florida’s past should help shape the decisions we make today. Baker will touch on 12,000 years of Florida history in an entertaining, fast-paced and approachable manner. He will walk you through a timeline of the risk takers, entrepreneurs and dreamers who helped to shape a modern Florida. Doors open at 5:30 p.m., lecture begins at 6 p.m. The lecture is at the Keys History & Discovery Center and Islander Resort Conference Center, MM 82. Snacks and a cash bar will be available. Reservations are strongly recommended.
Contact: 305-922-2237
Email: [email protected]

October 23,  in Key West
Fantasy Fest Pet Masquerade
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.
Email: [email protected]

October 24,  in Key Largo
Friends of the Key Largo Cultural Center presents: Ocean Life Series
This month's speaker, Dr. Douglas Wartzok, shares underwater acoustics: marine mammals, seismic and sonar. Ocean Life Series events are free and open to the public. Meet and greet at 6:30 p.m., at Murray Nelson Cultural & Government Center, mile marker 102. Lecture series from 7-8 p.m.

October 25,  in Islamorada
Florida Keys Wild Bird Center presents: Owl-O-Ween
From 5-8 p.m, enjoy spooktacular fun for the whole family, while benefiting a local organization committed to protecting Keys wildlife. Activities include fun & educational games, trick-or-treating, face painting, arts and crafts. Drinks and snacks will be served. Donations of $5/pp or $10/family greatly appreciated. Located at Laura Quinn Wild Bird Sanctuary, 93600 Overseas Highway, near mile marker 93 bayside.

October 25 to October 26,  in Islamorada
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
Email: [email protected]

October 25,  in Key West
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.

October 26,  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.

October 26,  in Key West
Old Island Restoration Foundation presents: Fantasy Fest Porch Party
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 26,  in Big Pine
'A Screaming Green Halloween' at the Key West Tropical Forest
Staged at the Historic Key West Tropical Forest & Botanical Garden, from 10AM – 2PM for children to have a fun and safe 'Trick or Treat.' Arts, crafts, bounce house, games, food and candy stations are to be set up throughout the garden so kids can be in costume, explore the Garden and participate in tricks and the hunt for treats while learning how to save the environment and respect nature! Two costume competitions with prize categories for ages 5 and under & 6–12. Costume judging begins at Noon with prizes awarded for Best Recycled Costume, Best Theme Costume & Most Original Costume. Special attention given to costumes made of recycled materials. The Garden is located at 5210 College Road on Stock Island.

October 27,  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 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.
Contact: Farmer Jeanne Selander 305-293-7300

October 28,  in Key West
The Allman Betts Band With Special Guest Jd Simo At Sunset Green Event Lawn
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 to November 02,  in Big Pine
Sugarloaf Showdown Inshore Fishing Tournament
Hosted by the Lower Keys Guides Association to benefit the Guides Trust Foundation, this new inshore two-person team tournament targets barracuda, bonefish and permit. Open to all anglers and guides. Headquartered at the Sugarloaf Marina, and social events at the iconic Sugarloaf Lodge Tiki Bar.
Contact: Lisa Booker 850-688-3244
Email: [email protected]

October 31,  in Key West
Annual Halloween Conch Train
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.
Contact: Ms. Bennett 305-294-1296 or 305-517-6611
Email: [email protected]

October 31,  in Key Largo
Free Fish Identification Class wth REEF
Want to improve your fish identification knowledge? Join us each month for a free fish identification class in REEF's Interpretive Center, led by REEF volunteers Carlos and Allison Estape. Each month, on the last Thursday, Carlos and Allison share insights on Tropical Western Atlantic fish identification and behavior. Class is free and open to the public. Set for 7 PM at REEF Interpretive Center, 98300 Overseas Hwy, near mile marker 98 in the median.

January 26 to October 08,  in Key West
Impromptu Classical Concerts presents: Trio Gaspard
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.

The Lodging Association of the Florida Keys and Key West
818 White St.
Suite 8
Key West, FL 33040
  305-296-4959 phone
305-296-1408 fax
[email protected]

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