Events & Festivals

Nov 4, 2021 – Jan 31, 2022
Arts Council presents 2021 Members Show ‘Dazzling Horizons’
The Opening Reception will be held Nov. 4, from 5:30 – 7:30 pm at the historic Gato Building, 1100 Simonton St. The exhibition will remain on display through January 2022. Dazzling Horizons – a look forward and a look around – the creativity is inspirational! Our magnificent sunsets, colorful skies, shiny moon, and endless glistening waters encourage us to preserve and enjoy nature.

Dec 29, 2021 – Jan 15, 2022
Fringe Theater presents: Diva! Live From Hell
The high school drama club president literally kills for a role and finds himself starring in a “flaming hot” cabaret presented nightly — live from hell. Wickedly fun. Tickets, show dates and times online. Performances begin at 7 p.m., Fringe Theater, 600 White St.

Jan 6, 2022 – Jan 8, 2022
Pole Vault in Paradise Competition
Pole Vault in Paradise brings together pole vaulters from age 9 to 75 to compete alongside some of the best pole vaulting elites from around the country. Sponsored by the nonprofit Key West Track & Field Club, the event is to be staged at Higgs Beach. Prize monies for male and female challengers are up for grabs, including additional prize money for any man or woman who breaks the island record.

Jan 13, 2022 – Jan 16, 2022
Key West Kingfish Mayhem
This the first tournament of the five-leg Kingfish Mayhem Pro Series. In the winter, Key West is the staging ground for King Mackerel before they start their annual migration in the Gulf. Big fish from the 50-70 lb. range are common in these areas, which creates an exciting and competitive environment at the weigh-in. This event has been enhanced by adding tuna, mahi and wahoo, for a four-species tournament. Teams from all around travel to join this world-class event for their shot at claiming King of Key West!

Jan 15, 2022 – Jan 16, 2022
16th Annual Florida Keys Seafood Festival
Bring the whole family for the freshest seafood caught, cleaned, prepared and served by local fishermen. A $10 admission is good for BOTH Saturday and Sunday. New location this year is to be at Truman Waterfront Park at the end of Southard Street. This event is a fundraiser for the Florida Keys Commercial Fishermen’s Association FKCFA and goes to support sustainable fishing programs, marine restoration projects & college scholarships.

Jan 15, 2022 – Jan 16, 2022 Key West
Key West Half Marathon & 5k Run
Recognized by Runners World magazine as one of the 10 great half-marathons of the winter season, the race follows a 13.1-mile course that includes Old Town Key West and the scenic waterfront. The race typically attracts American and international runners to compete in Key West’s balmy January climate. Named as one of the United States’ leading winter half marathons, Best Destination Half Marathons and Bucket List Best Half Marathons, is ranked among 13 must-do U.S. half-marathons by

Jan 24, 2022 – Jan 31, 2022
Kelly McGillis Classic
Women from countries far and wide will be descending upon Key West for flag football competition, fun and learning. It is anticipated this event is to have the most international countries represented, and organizers are expecting teams from USA, Morocco, Spain, Mexico, India, Jamaica, Honduras, El Salvador, and Sweden.

Feb 10, 2022 – Feb 12, 2022 Key West Fishing
Cuda Bowl
The toothy barracuda are prey for competitors in this annual challenge. The all-release flats tournament got its name because it’s scheduled each year just before the Super Bowl NFL football championship. Fishing is scheduled Friday and Saturday and must not exceed eight hours per day. Anglers and guides can leave from and return to the marina of their choice, but rules mandate that by 5:30 p.m. each day they must bring their catch forms and photos of fish caught to the Hurricane Hole Marina.

 Feb 17, 2022
25th Anniversary Gala of the Community Foundation of the Florida Keys
Join your Community Foundation in celebrating 25 years of serving the Keys by connecting people, resources, and needs through philanthropy. Dance the night away with the Prime Movers. Ticket and other information online.

Feb 18, 2022
Honky Tonk Heartbreak: A Classic Country-and-Western Burlesque Revue
Key West Burlesque pays tribute to the classic country-and-western songbook in a down-home and dirty burlesque extravaganza. Featuring a live band of local C&W musicians, Honky Tonk Heartbreak: a Country-and-Western Revue is an anthology of stories, songs, and striptease. Doors open 7PM, show starts 8PM at Key West Theater, 512 Eaton St.

Feb 26, 2022
38th Annual Key West Headdress Ball

Kick off Mardi Gras season at the Coffee Butler Amphitheater, Truman Waterfront Park for the outdoor gala, rescheduled from October due to coronavirus concerns. Doors open 6:30 p.m., show starts 8 p.m. Sponsored by the Key West Business Guild. Tickets for purchase online. Ticket holders from 2021 event can carry over.

Dec 14, 2021 – Mar 24, 2022
Southernmost Chamber Music Society 2021-22 Season
The Dec. 14 concert celebrates the holidays with Keys Choral Arts! Other concerts of the season include a January concert featuring music from the baroque period, with composers like Bach, Handel, Soler and others. February welcomes the Classic and Romantic periods, Mozart, Brahms, Schubert, and others. In March, the French romantic literature. Performance dates: January 20; February 24; March 24. Guest musicians have been invited to join throughout the season, both local and from across the country. Concerts will be on Thursday evenings at 7 p.m., held in the Parish Hall at the rear of the property of St Paul’s Episcopal Church, 401 Duval St.

Mar 1, 2022 – Mar 31, 2022
Tennessee Williams Birthday Celebration
Internationally renowned playwright Tennessee Williams, who lived in Key West for more than 30 years, once said of his chosen home, “I work everywhere, but I work best here.” Fans of Williams’ classic plays can explore his writing and life in the island city. While the festival’s traditional receptions won’t take place because of coronavirus concerns, the schedule includes screenings of films adapted from Williams’ works, prose and poetry contests and an online program of readings and reminiscences. In addition, private tours of Key West’s Tennessee Williams Museum, located at 513 Truman Ave., are offered by appointment.

Mar 7, 2022 – Mar 10, 2022
March Merkin Invitational Permit Tournament
This charity flats-and-fly-only tournament challenges anglers to catch, tag and release silvery permit to vie for elite titles. The event is traditionally held at the Key West Harbour Yacht Club on Stock Island, and features a silent online auction.

Apr 14, 2022 – Apr 24, 2022
Conch Republic Independence Celebration
Every year visitors join Florida Keys residents for the Conch Republic Independence Celebration, a quirky event honoring the birth of the republic and its place in Keys history. The republic was founded in April 1982 to protest the installation of a U.S. Border Patrol checkpoint that stopped traffic at the top of the Florida Keys Overseas Highway, the only road in and out of the Keys.

Apr 30, 2022
Papio Kinetic Sculpture Parade
A people-powered parade of colorful mobile structures rolls through Key West’s historic downtown intended to intrigue and inspire fans of creative recycling and ‘outsider’ art. The event is an artistic, creative way to raise awareness about the legacy and the importance of artists in the Florida Keys while using recycling as a key component.

Jun 1, 2022 – Jun 5, 2022
Key West Pride
Presented by the Key West Business Guild, events showcase the diversity and welcoming atmosphere that make the southernmost city a top vacation destination for LGBTQ visitors. The festival schedule typically includes pool parties at guesthouses and emporiums, drag shows by Key West’s top performers, a street fair on famed Duval Street, nighttime soirees at local clubs, a burlesque-style show with an LGBTQ flair and the lively “Rainbow Roast.”

Jun 15, 2022 – Jun 19, 2022
I Love Stock Island Festival
This five-day festival is to feature one-of-a-kind Stock Island-inspired activities and authentic immersive experience in local community, culture, and art. It’s a great way to celebrate Father’s Day weekend with friends and family in the laidback atmosphere of Stock Island, just across the Cow Key Channel Bridge from Key West.

Jun 17, 2022 Key West
CFK Swim Around Key West
Embark on an adventurous swim – a 12.5 loop around the island with fantastic landscape views of Key West and swimming in the pristine waters. Compete in different categories of either a solo swimmer, a solo swimmers with fins, a solo swimmers using a mermaid tail or a monofin or gather your friends and compete in the relay category of a 2-person, 3-person, 4-person, 5-person or 6-person teams. Not interested in the full island swim? Try some of the smaller races offered, a 6.1-mile swim, a 2-mile swim, a 1-mile swim or an 800-yard swim.

Jun 23, 2022 – Jun 26, 2022
Fifth Annual Mango Fest
Experience all things Mango through shopping, education and demonstrations. Stroll virtually through a vendor village, enter a poetry contest, photo contest, see virtual culinary and cocktail demos, and more. Details to come for the 2022 event.

Jul 20, 2022 – Jul 23, 2022
Stock Island Marina Village Key West Marlin Tournament
Anglers ply the waters once fished by novelist Ernest Hemingway, vying for $50,000 in guaranteed cash prizes. Held in conjunction with Key West’s annual Hemingway Days festival, the event awards $25,000 to the first-place team. Teams can enter one fun fish (dolphin, tuna, wahoo or released sailfish) per day to add to their point total.

Aug 11, 2022 – Aug 14, 2022
26th Annual Key West Lobsterfest
Seafood lovers can chow down on Florida’s clawless lobster during a tasty “feast-ival” that features a savory schedule of events ranging from a traditional lobster boil to a lively street fair starring the sensational crustacean prepared in a variety of ways. The flavorful festivities celebrate the bounty of the Florida Keys lobster season that opens Aug. 6. Famous for its sweet and tender meat, the Keys’ spiny lobster often is served steamed with drawn butter, paired with a seasoned stuffing or cold in savory salads.

Sep 1, 2022 – Sep 5, 2022
Key West Brewfest
Fans of beers and ales can sample about 150 of them while also discovering the flavors of the continental United States’ southernmost island. Activities ‘on tap’ include brew-focused dinners, pool parties and brunches, the lavish BrewFest Tasting Festival held Saturday on Key West’s South Beach and other enticements.

Sep 7, 2022 – Sep 11, 2022
Womenfest Key West
The popular festival for lesbians and their friends is designed to allow singles, couples and groups of women to experience the atmosphere of openness and acceptance that has made Key West an internationally acclaimed lesbian and gay vacation destination.

Oct 21, 2022 – Oct 30, 2022
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. The 2022 theme is ‘Cult Classics and Cartoon Chaos.’

Dec 31, 2022
Schooner Wharf “Rigging” in the New Year!
The event is emceed by Key West magician Frank Everhart and radio personality Bill Hoebee. Hoist your drink – and your eyes – toward the top of the towering mast as the countdown begins and another year ends.