Events & Festivals

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.

Nov 2, 2019
27th Annual ABC 5K Walk/Run
Sponsored by Zonta, this running race benefits women’s health screenings and breast cancer awareness in the Lower Florida Keys. Race begins and ends at Salute on Higgs Beach. Registration is at 7am and start time is 8am from race start/finish at Salute! 1000 Atlantic Blvd in Key West. All participants receive a participation medal and the first 400 registrants will get a t-shirt . Register early! Per person cost is $25 in advance until Oct. 18, $30 after Oct. 18 and $35 day of race.

Nov 3, 2019 – Nov 11, 2019
Waterfront Playhouse presents: The Informer
A teacher and his wife terrified that their son, a fanatic member of the Hitler Youth, will denounce them for their critical comments about the regime. Showtimes 7 p.m., tickets online.

Nov 3, 2019 – Nov 10, 2019
Key West Powerboat Races
High-speed offshore powerboats race in Key West in this annual challenge, known internationally as the Indianapolis 500 of powerboat racing.

Nov 20, 2019 – Nov 24, 2019
Key West Film Festival
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 27, 2019
Lighting of the Bight: Key West Harbor Walk of Lights
Gather on the Harbor Walk plaza at Greene and Elizabeth St. to best see the official lighting of the 2019 Key West “Harbor Walk of Lights”with more lights and creative displays than last year, all continuing the “Maritime History of Key West” theme! The Key West “Harbor Walk of Lights” traditional main features will light up that night, including the Fishing Buoy Tree, a fresh pine Nautical Christmas Tree and the original Key West Lobster Trap Tree. Harbor Walk of Lights, lit nightly through New Year’s Eve, stretches along the Key West Historic Seaport and Key West Bight Marina.

Dec 4, 2019
Key West Lighted Bike Ride
The Lighted Bike Ride helps to gather the needed toys for the struggling, working families of Key West for the holidays. Families and individuals with lighted and decorated bikes ride through the streets for the community to see. Entry for the bike ride is an unwrapped toy or monetary donation for Holiday Helpers. Wesley House Family Services coordinates this bike ride – registration begins October 1 online. This year the Coke Florida Caravan will be in Bayview Park to provide free photos with Santa along with cookies (from Winn Dixie) and milk – 5pm – 7:30pm. The Lighted Bike Ride will leave Bayview Park at 7pm Entry fee for the Bike Ride is one unwrapped toy for Holiday Helpers or monetary donation

Dec 7, 2019
TRIKW Sprint & Olympic Triathlon
The Key West Triathlon expects up to 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. Event highlights feature an Aquabike competition this year, along with a .76 km Atlantic Ocean swim from Higgs Beach, a 20km U.S. 1 cycling ride along South Roosevelt Boulevard and a 5km run along Smathers Beach.

Dec 14, 2019
Sixth Annual Parade of Paws and Shopping Bazaar
Bring your dogs, wear a t-shirt with a picture of your kitty with pride, or walk with a paddle displaying your pet’s photo! Shopping Bazaar inside the dog park features entertainment, food vendors, a Kissing Booth, holiday gifts for that special snuggle bug and more! A unique opportunity to support the lifesaving mission caring for the Keys’ community’s homeless animals, the event supports the Florida Keys SPCA. Check in is 9 a.m. Event is from 10 a.m. to 2 p.m., Higgs Beach, at the Higgs Dog Park. Bring four-legged friends to meet the reigning King and Queen.

Dec 18, 2019
Key West Art & Historical Society Hosts Holiday Concert & Bazaar at Custom House Museum
From 5-9 p.m., located on the sweeping historic porch and walkway of the Custom House Museum. The immensely popular celebration will feature some of Key West’s finest artisans, musicians and choirs, food and libations, free entrance to the museum and its two stories of exhibits, and a dazzling holiday light show of magical vector projections on the face of the Custom House. Browse hundreds of unique gift options while enjoying the music, food and libations on and around the island’s architectural crown jewel, with eggnog to lift the frazzled ‘final shopping days’ spirits and Santa on hand for last minute requests and ‘selfie’ photos.

Dec 27, 2019 – Dec 28, 2019
60th Annual Key West Home Tours
Presented by the Old Island Restoration Foundation, the annual self-guided tours from 3-6 p.m. each day showcase festively dressed Key West homes and gardens. Tickets are $35 in advance, $40 day-of-tour. You will be enchanted by exquisite restorations, creative renovations and delightful interiors featuring art collections, antiques, and much more. All proceeds from the tours stay in the Key West local community fulfilling OIRF’s mission of “Celebrating and sustaining Key West’s unique architecture, culture and history.”

Dec 31, 2019 – Jan 1, 2020
New Year’s Eve Shoe Drop Celebration
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.

Dec 31, 2019
Schooner Wharf “Rigging” in the New Year
The popular waterfront watering hole once again will present its nautical New Year’s Eve tradition with “The Lowering of the Pirate Wench” from the towering mast of the tall ship America 2.0 docked in front of the bar in the Key West Bight. Everyone’s favorite pirate wench and co-owner of Schooner Wharf Bar, Evalena Worthington, will descend dramatically against large, illuminated countdown numbers. The stroke of midnight will signal the start of 2020 with cannon fire and the jubilant sound of horns and noisemakers from the crowd against a backdrop of the ship’s crew dressed as pirates.