Key West Events

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SoMo Marathon & Half Marathon
SoMo Marathon & Half Marathon
Oct 5 – Oct 7 all-day
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 …

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39th Annual Key West Fantasy Fest
39th Annual Key West Fantasy Fest
Oct 19 – Oct 28 all-day
39th 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.  …

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Goombay Festival
Goombay Festival
Oct 19 – Oct 20 all-day
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 …

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Celebrate 75 Years of Aviation at Marathon Airport!
Celebrate 75 Years of Aviation at Marathon Airport!
Oct 20 all-day
Celebrate 75 Years of Aviation at Marathon Airport!
Fly or drive to the celebration! This free-admission event from 9 a.m. to 5 p.m. is to commemorate 75 years of aviation in the heart of the Florida Keys. Discover the Aviation Museum, see historic …

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Eighth Annual Stone Crab Claw Eating Contest
Eighth Annual Stone Crab Claw Eating Contest
Oct 20 all-day
Eighth Annual Stone Crab Claw Eating Contest
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 …

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Rams Head Productions presents: Michael Franti & Spearhead 6:00 pm
Rams Head Productions presents: Michael Franti & Spearhead
Oct 22 @ 6:00 pm – 10:00 pm
Michael Franti is a musician, humanitarian, and filmmaker who is recognized as a pioneering force in the music industry. Franti believes in using music as a vehicle for positive change and is revered for his …

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Fantasy Fest Pet Masquerade
Fantasy Fest Pet Masquerade
Oct 24 all-day
Fantasy Fest Pet Masquerade
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 …

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36th Annual Headdress Ball
36th Annual Headdress Ball
Oct 25 all-day
36th Annual Headdress Ball
The Key West Business Guild presents this premier gay and lesbian event of the Fantasy Fest celebration, proudly opens the new Key West Amphitheater at the Truman Waterfront Park. Tom Luna returns as the outrageous …

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Bud Light Fantasy Fest Parade
Bud Light Fantasy Fest Parade
Oct 27 all-day
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, …

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Third Annual Marathon’s Fall Harvest at Crane Point Museum
Third Annual Marathon’s Fall Harvest at Crane Point Museum
Oct 28 all-day
Third Annual Marathon’s Fall Harvest at Crane Point Museum
From 4-8 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 …

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