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Key West Events

Event calendar courtesy of fla-keys.com - The Tourism & Development Councel of the Florida Keys

Events in Key West for October, 2016

Year:  Month: 
April 09 to November 30,  in Key West
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: Rob Harris 305-587-6718
Email: director@keywestfishingtournament.com
September 16 to October 16,  in Key West
WineDine KeyWest
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 06 to October 09,  in Key West
SoMo Marathon & Half Marathon
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 13 to October 22,  in Key West
Christopher Peterson's EYECONS
A master of impersonations, both visually and vocally, with impeccable comic timing. The show is all LIVE, no lip-sync. Thrill to his parodies of Marilyn Monroe, Carol Channing, Madonna, Joan Rivers, Reba McEntire, Bette Midler, Tina Turner, Julie Andrews, Barbra Streisand, Liza Minnelli, Judy Garland, Eartha Kitt, Cher, Bette Davis, Lucille Ball, even Lady GaGa. Show dates are 10/13, 10/18, 10/22. Show times 9 p.m., at La te da 1125 Duval St.
Contact: 305-296-6706
October 15 to October 16,  in Key West
Fifth Annual Standup Paddle Invitational 2016
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 16,  in Key West
Key West Halloween Half Marathon and 5K Run
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 19,  in Key West
Key West Theater presents: The Nighthawks
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 21 to October 30,  in Key West
37th 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 2016 festival theme is "Political Voodoo and Ballot-Box Barbarians."
Contact: 305-296-1817
Email: info@fantasyfest.net
October 21 to October 22,  in Key West
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.
October 21 to October 26,  in Key West
Peter Pan's Adventures in Naughty Land: A Burlesque Parody
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 22,  in Key West
Key West Theater presents: Psychedelic Furs
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 23,  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 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 26,  in Key West
Fantasy Fest Pet Masquerade
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 27,  in Key West
The Smallest Parade In The Universe
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 27,  in Key West
34th Annual Headdress Ball
The glamorous gala is to be held under a gigantic tent at Key West's Truman Waterfront, located at the end of Southard Street beyond Truman Annex. Entrants wearing elaborate masks, cowls, bonnets and other headgear — many decorated with feathers, sequins and unexpected or bizarre accessories — are to vie for cash prizes at the head-turning event. Some headdresses in past years have featured moving parts, while others tower far taller than their wearers.
October 28,  in Key West
Fantasy Fest Masquerade March
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 31,  in Key West
Key West Theater presents: Little River Band
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