Florida Keys
Calendar of Events for October  
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October 23,  in Key West
Zombie Bike Ride
October 23
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 and tree-lined streets 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 31,  in Marathon
Trick or Treat with the Cranes
October 31
Costumed goblins and ghouls can enjoy some frightening fun at the beautiful 63-acre Crane Point Hammock, located at mile marker 50.5 bayside in Marathon, from 5-8 p.m.
Contact: 305-743-3900

October 21 to October 26,  in Key West
Peter Pan's Adventures in Naughty Land: A Burlesque Parody
October 21 to October 26
Peter Pan's Adventures in Naughty Land: A Burlesque Parody is a grown-up version of one of the world's most beloved stories. The always-outstanding Key West Burlesque performers and an array of special guest stars including Cheeky Derrière, Moana Amour and Aurora Natrix, portray the cast of the cherished tale like you have never seen them before. Performances at Waterfront Playhouse. Doors open at 7:30 p.m., show begins at 8 p.m.
Contact: 305-294-5015

October 09,  in Marathon
Marathon's Fall Harvest at Crane Point Museum
October 09
From 4-7 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

October 22,  in Key West
Key West Theater presents: Psychedelic Furs
October 22
Alternative rock lovers, this show is for you! Led by vocalist and songwriter Richard Butler, and his bass-wielding brother Tim, the Furs scored major hits with "Love My Way," "Pretty In Pink," "Heaven," "The Ghost In You," and "Heartbreak Beat" in all releasing seven studio albums, spawning several compilations, a boxed set, and a live concert DVD. Show time 8 p.m.
Contact: 305.985.0433
Email: boxoffice@thekeywesttheater.com

October 31,  in Key West
Key West Theater presents: Little River Band
October 31
Little River Band was the first Australian band to successfully conquer foreign markets from an Australian base. Fans of the band are treated to an entertaining mix of classic songs and new material, delivered as always with that trademark LRB blend of impeccable vocals, soaring harmonies, kick-ass playing and the unmistakable feeling of a band really enjoying itself. Show time 8 p.m.
Contact: 305.985.0433
Email: boxoffice@thekeywesttheater.com

October 01,  in Marathon
The Marathon Games
October 01
Join a five-event, Keys style Pentathlon, featuring swimming, kayaking, standup paddling, driving frozen "golf" balls and a footrace. Intrigued? Hosted by the new Florida Keys Country Club, proceeds from this uniquely Keys event are to support local nonprofits. Single and two-person team athletes can register.

October 22,  in Key Largo
Fall Festival & Grow Show
October 22
From 10 a.m. to 4 p.m., presented by the Garden Club of the Upper Keys, located at Francis Tracy Garden Center, MM 94 Bayside. Start your holiday shopping with unique hand made gift items. Heirloom holiday decorations, placemats, ornaments, handmade jewelry, decorated flower pots, garden stepping stones, + many more one-of-a-kind items. Grow Show includes free mini-classes, every 45 minutes all day, plus a Master Gardener plant clinic. Games and activities for kids include a costume parade with prizes, pony rides and more.
Contact: Beverly (305) 451-8137
Email: deborrajonas@bellsouth.net

October 21 to October 22,  in Marathon
Marathon Community Theater presents: One Weekend Only
October 21 to October 22
Join the theater's annual fundraiser, "One Night Only," a variety show of MCT MISCAST to any production you are unable to be cast for by race, gender, age, etc. Followed by a gala party with champagne & appetizers.
Contact: 305-743-0994

October 15 to October 16,  in Key West
Fifth Annual Standup Paddle Invitational 2016
October 15 to October 16
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. Register online.

October 28,  in Key West
Fantasy Fest Masquerade March
October 28
Thousands of costumed revelers are to parade through Key West's historic Old Town during the offbeat Masquerade March that begins at the local cemetery. The march is a highlight of the island's annual Fantasy Fest celebration, a lavish pre-Halloween masking and costuming festival scheduled Oct. 21-30. Themed "Political Voodoo and Ballot-Box Barbarians" in an offbeat salute to the upcoming U.S. presidential election, Fantasy Fest offers a 10-day roster of more than 40 elaborate events.

October 12 to October 16,  in Key Largo
Fourth Annual Humphrey Bogart Film Festival
October 12 to October 16
The fourth annual 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.

October 07 to October 09,  in Key Largo
Fifth Annual Downtown Key Largo Songfest
October 07 to October 09
A host of elite Nashville songwriters are to liven up Key Largo stages during this Columbus Day weekend festival that features music in genres including jazz, blues, rock and roll, country and contemporary pop. In addition, music lovers can enjoy the stories behind yesterday's favorites and today's popular hits.
Contact: Robert DiGiorgio 305-619-0172
Email: downtownkeylargo@gmail.com

October 16,  in Key West
Key West Halloween Half Marathon and 5K Run
October 16
Many participants wear costumes ranging from eerie to exotic as they travel the flat, fast course through Key West's Old Town and scenic waterfront areas. Runners in the half marathon, set to start at 6:30 a.m. Sunday, chart a 13.1-mile course beginning at the Schooner Wharf Bar, 202 William St. in the Historic Seaport. They are to proceed around the island, including its Gulf of Mexico and Atlantic Ocean shores, before ending where they began.
Email: halloweenhalf@exclusivesports.com

October 26,  in Key West
Fantasy Fest Pet Masquerade
October 26
The eccentric competition is likely to include Re-pup-licans and Demo-cats as well as other canine, feline and avian critters strutting their stuff on an oceanfront stage. Political "party animals" can compete for costume prizes and glory Thursday during soirees including a tantalizing toga party that is one of the festival's longest-running events.
Email: petmasquerade@hotmail.com

October 22,  in Marathon
Sixth Annual Stone Crab Claw Eating Contest
October 22
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 and two-person teams must be at least 18 years old to enter.
Contact: 305-743-4353
Email: keys.fisheries@comcast.net

September 30 to October 01,  in Islamorada
9th Annual Mad Dog Mandich Inshore & Offshore Fishing Classic
September 30 to October 01
Anglers compete in an offshore division targeting dolphin, kingfish, tuna, wahoo, snapper and grouper; and new this year is an inshore division in which anglers compete for mangrove snapper, spotted sea trout, redfish, snook and tarpon. A portion of the proceeds of this boat/team tournament are to benefit Mariners Hospital Oncology Services. Headquartered at Postcard Inn Beach Resort & Marina. Top Offshore and and Inshore division cash prizes.
Contact: Leah 305-667-0399
Email: leah@maddogclassic.com

October 06 to October 09,  in Key West
SoMo Marathon & Half Marathon
October 06 to October 09
Presented by Pat Croce's Rum Barrel, 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 include the race and a Sunday Paddle Board race for the Special Olympics of Monroe County.
Contact: 305-766-5284
Email: liz@somomarathon.com

October 21 to October 22,  in Key West
Goombay Festival
October 21 to October 22
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.

October 21 to October 23,  in Islamorada
Ladies Let’s Go Fishing!” Annual Keys Fishing University for Women
October 21 to October 23
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 lighthearted yet skill-heavy curriculum to learn and hone abilities in offshore, bottom, inshore and fly fishing.
Contact: Betty Bauman 954-475-9068
Email: fish@ladiesletsgofishing.com

October 07 to October 09,  in Islamorada
Robert James Sales Baybone Celebrity Tournament
October 07 to October 09
The second tournament in the Redbone Trilogy, now headquartered in Islamorada at Pelican Cove, 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
Email: susan@redbone.org

October 29 to October 30,  in Islamorada
Fall Backcountry Fly Championship Series
October 29 to October 30
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.

October 14 to October 15,  in Islamorada
15th Annual Casting for Cats Fishing Tournament
October 14 to October 15
Headquartered at the Islander Resort, this popular one-day tournament proceeds have always and will continue to go to the spaying/neutering of the feral cat population in the Keys. Casting for Cats is a 501C-3 charity. Entry is only $175 per angler, and social tickets are $20 for Friday night, $30 for Saturday night dinner and award celebration. Kickoff party is Friday, with final registration.
Contact: Sharon Ellenwood 305-664-2012
Email: sharellen@netzero.net

October 22,  in Islamorada
Matecumbe Historical Trust presents "29 Points of Interest" Historic Trolley Tour
October 22
Enjoy an enlightening trolley ride through time. Guided trolley tours depart at 10 a.m. from the Islamorada Moose Lodge, MM 81.5. The one-hour, colorful and much acclaimed historical tours feature 29 points of interest on the islands of Islamorada. Tickets may be purchased on site or call in advance. Adults are $15, children six and under are free.
Contact: Barbara Edgar 305-393-0940

October 19,  in Key West
Key West Theater presents: The Nighthawks
October 19
When Mark Stutso, master of the deep groove, joined The Nighthawks at the beginning of 2010, the 21st-century version of the legendary American roots band was complete. With Paul Bell and Johnny Castle in the band for nearly a decade, and founding father Mark Wenner the remaining original, this team outshines all previous incarnations. Show starts 8 p.m.

October 20,  in Islamorada
Oktoberfest! Third Thursday Art Walk
October 20
Showcasing the fine arts, music and culinary nuances of the Purple Isles, the Morada Way Arts & Cultural District features national and local artisans, showcased in galleries between mile marker 81 and 82. Oktoberfest features "culinary art" and live music with beer from Florida Keys Brewing Co., the local-only brewery at Morada Way. from 6-9 p.m. Free admission. Art Walk is held the third Thursday of each month.

October 19,  in Islamorada
History of Diving Museum's Immerse Yourself! Lecture Series: Mystery of the Last Olympian
October 19
A free lecture series held at the museum, located at MM 82.9, every third Wednesday of the month at 7 p.m. Adventurers from treasure hunters to aquanauts help tell the story of mankind's attempts to explore, understand and venture under the sea. The evening lectures are informal, informative and provide a valuable educational resource at the museum, an acclaimed facility dedicated to the collection, preservation and display of relics and artifacts related to diving and its heritage.
Contact: 305-664-9737

October 21 to October 30,  in Key West
37th Annual Key West Fantasy Fest
October 21 to October 30
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 2016 festival theme is "Political Voodoo and Ballot-Box Barbarians."
Contact: 305-296-1817
Email: info@fantasyfest.net

September 16 to October 16,  in Key West
WineDine KeyWest
September 16 to October 16
Cuisine connoisseurs can enjoy multicourse prix fixe meals at as many as 30 Key West restaurants during WineDine KeyWest, billed as the island's first restaurant month. Restaurants include casual waterfront spots, trendy bistros, eateries specializing in fresh Florida Keys seafood and award-winning gourmet emporiums. Diners can register free online to take part in the month-long moveable feast.

October 27,  in Key West
The Smallest Parade In The Universe
October 27
A dazzling event from 5-9 p.m., at the corner of Caroline and William streets, at Key West Waterfront Brewery. Artists, craftsmen, model makers and creative types are encouraged to participate, making floats no larger than 18 inches! They are to "parade" down a replica of Key West's famed Duval Street while projections are flashed on the "street" to make them look like full-sized floats. Up to $2,000 in prizes. Event proceeds are to benefit the Monroe Association for ReMARCable Citizens, a nonprofit that provides life services for Monroe County's adult developmentally and intellectually disabled residents. Spectator tickets are $20 per person.

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

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Captain Jim Sharpe, Captain Michael Vaughn

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