Key West Events

Oct
5
Fri
2018
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 miles of ocean and gulf views, as well as iconic Key West landmarks. A full weekend of events including a 10k and 5k are planned.

Oct
19
Fri
2018
39th Annual Key West Fantasy Fest
Oct 19 – Oct 28 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. 

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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 recalling Key West’s Bahamian heritage. FREE event, noon to midnight both days.

Oct
20
Sat
2018
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 aircraft and enjoy discovery flights. Fun for all ages.

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 25 stone crab claws? Test your munching mettle at this zany contest. Individuals must be at least 18 years old to enter.

Oct
21
Sun
2018
Zombie Bike Ride @ Fort East Martello Museum
Oct 21 @ 2:00 pm – 3:00 pm

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 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.

Oct
22
Mon
2018
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 hi-energy live shows, inspiring music, and worldwide philanthropy efforts. Giving back has always been at the heart of Franti’s mission. He has dedicated his life to spreading the joy of music and positivity to millions of people. Doors open 5 p.m., show starts 6 p.m. at Sunset Green Event Lawn, 3820 N. Roosevelt Blvd.

Oct
24
Wed
2018
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 frisky pets and playful owners, all delightfully disguised, stroll, dance and even skateboard across a stage in a fun frolic for fame and fortune! Think you and your furry, feathered or slithery friend have the perfect outfit? Four categories to enter, $25 each entry; benefits the Lower Keys Friends of Animals.

Oct
25
Thu
2018
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 EmCee, with Rude Girl rocking out our sound.  Randy Roberts opens the show and is joined by some of the best of Key West local talent throughout the contest.  Over twenty-five contestants will parade their Headdress creations on the amphitheater stage to vie for the $3,000 first prize.

Oct
27
Sat
2018
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, dancers in bright feathered costumes and dazzling motorized floats. Join thousands of exuberant partygoers! It doesn’t get any wilder than this! Parade steps off at 7 p.m.; free to spectate.

Oct
28
Sun
2018
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 music. Admission is $5 for adults, $3 for children, free for ages 4 and under.

Nov
3
Sat
2018
Rams Head Productions presents: Lyle Lovett & Robert Earl Keen @ Rams Head Productions presents: Lyle Lovett & Robert Earl Keen
Nov 3 @ 6:30 pm – 9:30 pm

A singer, composer and actor, Lyle Lovett has broadened the definition of American music in a career that spans 14 albums. Coupled with his gift for storytelling, the Texas-based musician fuses elements of country, swing, jazz, folk, gospel and blues in a convention-defying manner that breaks down barriers. What separates Robert Earl Keen, an Americana music pioneer, from other songwriters is that he matches this lyrical literature with irresistible melodies, resulting in music that attracts thinkers and dancers alike. Doors open 6:30 p.m., show starts 8 p.m. at Sunset Green Event Lawn, 3820 N. Roosevelt Blvd.

Nov
4
Sun
2018
37th Annual Key West World Championship Races
Nov 4 – Nov 11 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
14
Wed
2018
Key West Film Festival
Nov 14 – Nov 18 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.

Nov
16
Fri
2018
Waterfront Playhouse presents: Carmen by Request
Nov 16 – Nov 17 all-day

Key West’s own “Conch Diva” returns to grace to stage bringing along some of your favorite performers. Showtimes 8 p.m.

The Avett Brothers at the Key West Amphitheater
Nov 16 @ 7:30 pm – 2:58 pm

Known for their live performances that blend bluegrass roots with the fierce fire of a rock show and an emotional, near-gospel spirit, The Avett Brothers are no strangers to major venues: for past summers, they have sold out three nights at Colorado’s legendary Red Rocks Amphitheater. They’re also a staple on the festival circuit, frequenting the likes of Bonnaroo and Shakey Knees. Gates open 6 p.m., shows start 7:30 p.m.

Nov
24
Sat
2018
Big Pine & The Lower Keys Island Art Festival
Nov 24 all-day
Big Pine & The Lower Keys Island Art Festival

Highlights of this holiday event, set for the Saturday after Thanksgiving each year, include live music by local entertainers, food, exhibits and booths featuring locally produced arts and crafts. Festivities traditionally take place on the grounds of the Lower Keys Chamber of Commerce, MM 31 oceanside.

Dec
1
Sat
2018
Key West Triathlon and Expo
Dec 1 all-day
Key West Triathlon and Expo

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
28
Fri
2018
59th Annual Key West House & Garden Tours
Dec 28 – Dec 29 all-day
59th Annual Key West House & Garden Tours

Presented by the Old Island Restoration Foundation, the annual self-guided tours from 3-7 p.m. each day showcase festively dressed Key West homes and gardens. Tickets are $30 in advance, $35 day-of-tour. Proceeds benefit the foundation’s museum and programs.

Jan
18
Fri
2019
59th Annual Key West House & Garden Tours
Jan 18 – Jan 19 all-day
59th Annual Key West House & Garden Tours

Tour elegant and unique private homes of Key West, ranging from exquisite restorations to creative renovations, and the interior design that complements each. January tours are offered 3 to 7 pm each day. Transportation between homes is available via Conch Train for $40 each, seating is limited. Tickets without transportation are $30 in advance and $35 on tour days. Proceeds benefit the foundation’s Oldest House Museum, grant and scholarship programs.