Events & Festivals
Aug 14, 2019 – Aug 18, 2019
The Key West Business Guild presents this all-male celebration that typically includes pool and dance parties, on-the-water adventures and a fashion show that raises money for a local non-profit organization.
Aug 29, 2019 – Sep 2, 2019
10th Annual Key West Brewfest
Nearly 200 beers and micro-brews are on tap at this “tasty” annual event that benefits the charitable efforts of the Key West Sunrise Rotary Club of the Conch Republic. Events from beer dinners, beer brunches, happy hour parties, pool parties, late-night parties, seminars and the Signature Tasting Festival Event (Aug. 31) are some of the offered activities.
Sep 4, 2019 – Sep 8, 2019
Each year thousands of ladies come together over the Labor Day weekend and stay for a wide range of activities and events during four days of revelry and fun. Key West welcomes women from across the globe to an annual celebration that has become one of the largest gatherings of lesbians and friends in North America’s Womenfest.
Sep 6, 2019 – Sep 8, 2019
Robert-James Sales S.L.A.M. Tournament
In the first of three tournaments in the annual Redbone Celebrity Tournament Series, also called The Trilogy, anglers target tarpon, permit and bonefish to achieve the coveted “flats grand slam.” The event raises funds for the fight against cystic fibrosis. A number of celebrities show their support by taking part in the tournament each year. Celebrity competitors have included Major League Baseball Hall of Famer Wade Boggs, former Denver Broncos football player Mark Cooper and former NASA space shuttle astronaut Bruce Melnick.
Oct 11, 2019 – Oct 12, 2019
SoMo Marathon & Half Marathon
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 18, 2019 – Oct 19, 2019
Bahama Village Goombay Festival
Held in Key West’s historic Bahama Village neighborhood, the lively, family-friendly 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 18, 2019 – Oct 27, 2019
40th 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.
Oct 20, 2019
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 in a deliciously scary spectacle. The wacky event begins at 2 p.m. and lasts until 6 p.m., as “Zombieland” opens at Fort East Martello Museum, a reputedly haunted historic site overlooking the Atlantic Ocean at 3501 S. Roosevelt Blvd.
Oct 23, 2019
Fantasy Fest Pet Masquerade
The eccentric competition is likely to include canine, feline and avian critters strutting their stuff onstage at the Key West Amphitheater. “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. Starts 6:30 p.m.
Oct 24, 2019
37th Annual Headdress Ball
The Key West Business Guild presents this premier gay and lesbian event of the Fantasy Fest celebration, at Key West Amphitheater at the Truman Waterfront Park. Some of the best of Key West local talent highlights the contest. Contestants parade their Headdress creations on the amphitheater stage to vie for a first-place cash prize.
Oct 25, 2019
Fantasy Fest Masquerade March
Famed as “the locals’ parade,” the march typically draws high-spirited revelers wearing everything from elaborate masks and costumes to offbeat creations inspired by the festival theme. Begins at the Key West Cemetery at Frances Street entrance but revelers can join the mad march anywhere along the two routes. Start marching at 5:30 p.m.; all are welcome; free admission.
Oct 26, 2019
Bud Light Fantasy Fest Parade
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.