Calendar

Oct
6
Fri
SoMo Marathon & Half Marathon
Oct 6 – Oct 8 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 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.

Oct
13
Fri
Sixth Annual Standup Paddle Invitational 2017
Oct 13 – Oct 16 all-day

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.

Oct
20
Fri
38th Annual Key West Fantasy Fest
Oct 20 – Oct 29 all-day

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 2017 festival theme is “Time Travel Unravels.”

Oct
27
Fri
The Smallest Parade In The Universe
Oct 27 all-day

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! Proceeds benefit the MARC house. Up to $2,000 in prizes.

Nov
5
Sun
36th Annual Key West World Championship Races
Nov 5 – Nov 12 all-day

Super Boat International returns with teams from all around the world who compete April through October in the National Series Points races and conclude in November for the famous Key West World Championships. High-speed offshore powerboats race in Key West Harbor and surrounding waters to continue Key West’s longstanding tradition in this annual challenge, known internationally as the Indianapolis 500 of powerboat racing. A portion of the 6.5-mile course runs through Key West Harbor, meaning smooth water where racers can achieve speeds above 140 mph and provide fans breathtaking displays of skill and power.

Nov
15
Wed
Key West Film Festival
Nov 15 – Nov 19 all-day

Showcasing films that exhibit excellence in storytelling, the festival’s lineup is to feature screenings and special events hosted at landmark venues throughout Key West, including the San Carlos Institute, Studios of Key West and Key West Theater. The four-day program is to include several films from multiple genres and categories as well as social events with filmmakers, actors and film lovers.

Dec
1
Fri
Key West Holiday Fest
Dec 1 – Dec 31 all-day

Each year a wide range of seasonal celebrations takes place throughout Key West during the month of December. Events include the lighting of the Harbor Walk of Lights, tours of historic decorated inns, a holiday parade and much more.

Dec
8
Fri
Inaugural Key West Grand Prix of the Sea
Dec 8 – Dec 10 all-day

Experience non-stop racing action as Sea-Doo, Yamaha, and Kawasaki personal watercraft racers take to the water averaging 75 mph. This race is the final round in 2017 and serves as the overall championship for the PRO Enduro and International Amatuer Championship. Jetcross Jet Ski stand up races will also be a part of this family friendly event free to the public.

Dec
9
Sat
Key West Triathlon and Expo
Dec 9 all-day

The Key West Triathlon and Expo expects to host a maximum of 1,000 participants and some of the sport’s best known triathletes; TRIKW allows you to bask in the warm weather and the waters of the Atlantic Ocean while the rest of the country is experiencing winter. Olympic and Sprint distances.

Dec
31
Sun
New Year’s Eve Shoe Drop Celebration
Dec 31 all-day

The Southernmost City celebrates with a descending 6-foot red high heel shoe carrying drag queen Sushi at the Bourbon Street Pub/New Orleans House complex, 724 Duval St. Seconds before midnight, the high heel bearing a lavishly gowned and coiffed Sushi is to be lowered from the second-story balcony of the complex toward the cheering crowds below. As midnight strikes and the New Year officially begins, she will land and gleefully pop the cork on a ceremonial bottle of champagne.

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