There is always something fun to do in Key West. This calendar of events is frequently updated.

Key West’s Most Complete Calendar of Events.

This calendar of events for Key West includes nearly every happening on the island throughout the year. Something missing? If you know of any Key West calendar events that we have overlooked please let us know by filling out this short form and we’ll quickly add it. Check back frequently: more events, dates, and details are added as the season progresses.

UPDATE:  Events are now being added to the 2022 event calendar.  We will add dates as events are confirmed.  If you have an event you would like to add to our calendar, visit this page to submit  your event details: https://www.keywesttravelguide.com/submit-your-event-for-the-key-west-calendar/

Quick links:  

  January 2022  |  February 2022  |  March 2022  |  April 2022  |  May 2022  | June 2022  |  July 2022  |  August 2022  |  September 2022  |  October 2022  |  November 2022  |  December 2022

2022 Key West Event Calendar

January 2022 Key West Events

• January 6 – 8, 2022 – SPORTS – Pole Vault in Paradise: Pole Vaulting Champions – Top national pole vaulters will perform their skills at Higgs Beach. FREE to attend.
• January 6 – 9, 2022 – LITERARY – Key West Literary Seminar – This year’s topic is “A Seminar Named Desire” Noteworthy and celebrated writers, including Judy Blume, Billy Collins, Jami Attenberg, Jericho Brown,  and numerous others gather at readings, discussions, lectures, and parties. Registration is now sold out, but a waitlist is available. More information is available at http://www.kwls.org/seminar or by calling 305-293-9291.
• January 13 – 16, 2022 – FISHING – Key West Kingfish Mayhem – Bet you didn’t know that the richest tournament prizes in saltwater fishing is for kingfish! Part of the mackerel family, this sportfish is known for its incredible striking speed. First-place prize is expected to be $15,000. For more information, call 954-605-8284 or visit https://www.meatmayhemtournamentsfl.com/key-west-kingfish-mayhem/
• January 15 – 16, 2022 – SPORTS – Annual Key West Half Marathon – Over 1000 runners enjoy near perfect temperatures, flat terrain, and Key West scenery in one of the most popular running races of the year. Entry fee costs between $50 and $120.00, depending on when you register and which race you choose. Call 305-296-7182 for more information. For more information visit https://www.keywesthalfmarathon.com
• January 15– 16, 2022 – FOOD – 16th Annual Florida Keys Seafood Festival – This festival celebrates Key West’s abundant fresh seafood with music & beverages served up by many of the Florida Keys commercial fisherman and families. Crab, lobster, ceviche, conch chowder, and other local cuisine is served up in a picnic setting. Entrance fee is $5 (children under 12 are FREE). 11 a.m. – 8 p.m on Saturday, 11 a.m. – 5 p.m on Sunday. Bayview Park at Truman Avenue and Eisenhower Drive, Key West. For more information, visit call 305-292-4501
• January 24 – 31, 2022 – SPORTS – Kelly McGillis Classic International Female Flag Football Championship & World Challenge – The world’s top female flag football players compete for championship titles.  For more information, visit https://iwffa.com/kelly-mcgillis-classic-2022/kelly-mcgillis-classic-2022-schedule-of-events/
• January 25 – 29, 2022 – MUSIC – Mile 0 Fest – Four-day music festival featuring major acts from the “Red Dirt & Americana” genre. Concerts will be held throughout Old Town, including the new Truman Waterfront Park Ampitheatre, and bars and clubs on Duval Street. Cost is $349 for 4-day festival pass. For more information and tickets, visit: https://www.mile0fest.com/ or call 877-412-7658.

February 2022 Key West Events

• February 10 – 12, 2022 – FISHING – Cuda Bowl – Cooler winter temperatures bring big barracuda up onto the saltwater flats, and catching them is a regular occurrence in this tournament. Last year 418 barracuda were caught and released. Tournament rules require artificial lures and flats boats only. Maximum 2 anglers per boat. Entry fee is $350 for two anglers. Hurricane Hole Marina on Stock Island. Visit https://www.cudabowl.com or call 305-360-6969 for more information.
• February 26, 2022 – LGBTQ – 38th Annual Key West Headdress Ball – Costume contest featuring dazzling headdresses created over many months and worn and displayed in this awe inspiring event. HUGE works of art, each more inventive and imaginative then the previous. Grand prize is $3000. Coffee Butler Amphitheater, Truman Waterfront Park.  Buy tickets early as this event sells out. More information at https://gaykeywestfl.com/headdress-ball/ or call 305-294-4603 for tickets.

March 2022 Key West Events

• March 1 – 31, 2022 – LITERARY – Tennessee Williams Birthday Celebration – Celebrating the former literary icon who resided in Key West.  Visit the museum devoted to the writer at 513 Truman Ave, by appointment.  For more information, visit https://www.kwahs.org/museums/tennessee-williams/twfestival
• March 7 – 10, 2022 – FISHING – Merkin Invitational Permit Tournament – Fly fishermen compete to catch Permit, one of the most challenging fish to catch on fly. Key West Yacht Harbor Marina (Stock Island). For more information, visit https://marchmerkin.com/ or call 303-888-4546.

April 2022 Key West Events

• April 14 – 24, 2022 – LOCAL COLOR – Conch Republic Independence Celebration – Celebration of Key West’s brief secession from the United States. Event highlights include bed races on Duval Street, conch shell blowing contest , arts & crafts show, Duval Street Parade , and the infamous bloody battle in Key West harbor where Conch Republic vessels toss stale cuban bread at Coast Guard vessels and each other in a mock secession. Kick-off party at the Schooner Wharf bar. For more information call 305-296-0213.
• April 30, 2022 – ARTS – Papio Kinetic Sculpture Parade – In recognition of Florida Keys artist Stanley Papio, known for his re-purposing of found objects into whimsical sculpture, this event showcases Key West’s creativity and whimsy with a parade of human-powered artworks. Competition categories include art bikes and kinetic sculptures. Parade begins at noon in front of Customs House at 281 Front Street. For more information, call 305-295-6616 or visit https://www.papioskineticparade.com/

May 2022 Key West Events

• May 4 – 8, 2022 – MUSIC – 26th Annual Key West Song Writers Festival – Features more than two-hundred top songwriters performing at a variety of venues in Key West, including a concert on the Sunset Pier of the Ocean Key House at 1 Duval Street and a free concert on Duval Street. For more information, visit http://www.keywestsongwritersfestival.com

June 2022 Key West Events

• June 1 – 5, 2022 – LGBT – Key West Pridefest – Event honoring diversity, openness and freedom in the city that is consistently recognized as one of the world’s top gay and lesbian vacation destinations. Includes a mix of: dance and cocktail parties, contests, shows, forums, activities on the water, tours, street fair and the Pride Parade along Duval Street. For more information, call (305) 292-3223 or visit https://gaykeywestfl.com/pride/
• June 17, 2022 – SPORTS – CFK Swim Around Key West – Swimmers circumnavigate the island of Key West, a distance of over 12 miles.  For more information, visit https://swimaroundkeywest.org/
• June 17 – 19, 2022 – SPORT – VFW Fishing Tournament – The whole family can participate in the fun event with prizes totalling $25,000.  Benefits disabled and in-need veterans of the Florida Keys. For more information visit https://www.vfwpost3911.org/tournament/
• June 23 – 26, 2022 – FOOD – 5th Annual Mango Fest Key West – As mango trees throughout the island are bursting with the succulent fruit, this festival celebrates all things mango, including tastings, art contests, and recipes.  For more information visit https://mangofestkeywest.com/

July 2022 Key West Events

• July 23 – 24, 2022 – SPORTS– Hemingway 5K Sunset Run & Paddleboard Race – Race and revel in a sports challenge.  For more information visit https://www.keywesthalfmarathon.com/hemingway-event-details/

August 2022 Key West Events

• August 10 – 14, 2022 – LGBTQ – Tropical Heat – All male, adults-only celebration of Key West’s gay community and lifestyle. Events include all-male themed parties and adult-oriented entertainment. For more information, visit https://gaykeywestfl.com/tropical-heat/ or call the Key West Business Guild at 305-294-4603.
• August 11 – 14, 2022 – FOOD – Key West Lobster Fest – Everyone will be partying on Duval Street, except the lobsters. Marking the official opening of lobster season, this crustacean-focused event features street fairs, live music, and arts & crafts. Street fair with free live concert on Saturday, noon-11pm, lower Duval Street. For more information, visit https://keywestlobsterfest.com/

September 2022 Key West Events

• September 1 – 5, 2022 – PARTY – Key West Brewfest – Labor-day weekend event featuring more than 150 different beers – including many award-winning microbrews. Events include seminars, tastings, pool parties, and meals. Big event is the Signature Tasting on Saturday,  at South Beach ($75 per person for that event, advance tickets required). For more information, visit https://keywestbrewfest.com/ or call 305-295-6519.
• September 7 – 11, 2022 – LGBTQ – Womenfest Key West – Lesbians and friends converge on Key West for a week of activities, including late night dancing, pool parties, comedy shows, sunset sails, competitive bull riding, and lots of music. Visit https://gaykeywestfl.com/womenfest/ or call 305-294-4603 for more information.

October 2022 Key West Events

• October 21 – 30, 2022 – PARTY – Key West Fantasy Fest – Week-long celebration and Key West’s biggest party of the year – with many adult-only events. This year’s theme is “Cult Classics and Cartoon Chaos”  In our opinion, Fantasy Fest is ready for a re-fresh, and we encourage you to be creative in your costume choice – not sleazy.  For more information, visit https://fantasyfest.com/

November 2022 Key West Events

December 2022 Key West Events

If you know of any Key West calendar events that we have overlooked please let us know by filling out this short form and we’ll quickly add it. And check back frequently – since more dates and details will be added as the season progresses.