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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 09 to November 30,  in Key West
Key West Fishing Tournament
April 09 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: Rob Harris 305-587-6718

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

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 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.

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.

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 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 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 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

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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