Events in the Florida Keys

Event calendar provided with the courtesy of the Monroe County Tourist Development Council.

Events in Florida Keys for 2022

  • August 24 - October 02 Islamorada
  • Florida Keys History & Discovery Center presents: 'The Study of Water' Exhibition
  • Website
  • The Florida Keys are an island oasis nestled in a sea of water. The Study of Water reveals four differing artistic expressions and intimate connections with water. Throughout the exhibition, each artist provides individual interpretations and personal associations with water. The works collectively reveal how water provides nourishment, sanctuary, and healing. Featured artists include South Florida and Florida Keys artists: Castro Humberto, Jul Jankowski, Derrick Crossland, and Lisa Lee Herman. Exhibit is open during business hours Tuesday-Sunday, 10am-5pm as part of museum admission through October 2, 2022. A gallery opening reception is to be held Aug. 24 from 5-7 pm. Admission is free and cash bar available.

  • September 06 - October 16 Key West
  • ‘Kids Free Florida Keys’
  • Website
  • Through Oct. 16, families can explore Florida Keys attractions, tours, watersports and other offerings with a value-added program that provides free admission or opportunities for children ages 12 and under. Download coupons for visits to nature-themed and historic attractions, restaurants and activities ranging from snorkel tours to aquarium explorations. The site features links to participating businesses and information about their offerings. Each child must be accompanied by at least one paying adult. Presented by the Key West Attractions Association.

  • September 29 - October 01 Key West
  • Comedy Key West Presents: Sally Brooks
  • Website
  • Hosted by Tom Dustin (Comedy Central, Winner of the Great Canadian Laugh-Off), Comedy Key West presents Sally Brooks, a nationally touring stand-up comedian, writer and podcaster know for her personal stories of misadventure and fun-loving, smart-assed nature. She is the cohost of Dumb Love, a comedy podcast about the dumb things people will do for love. Show starts at 8:30 p.m. Comedy Key West is located at 218 Whitehead St.

  • September 30 - October 01 Islamorada
  • Conch Scramble Charity Golf Tournament
  • Website
  • Floating greens, golf boats and biodegradable fish food balls highlight the annual “par-tee” on the water. Fans of golf and boating can expect to have a “hole” lot of fun honing their swings and raising money for charity one shot at a time. Teams of four and a designated boat driver “caddy” make stops at nine Islamorada waterfront venues and come ashore to tee off. Each player has two shots at the floating holes using biodegradable golf balls that dissolve into fish food after 90 hours in the water.

  • October 01 - October 01 Key West
  • 25th Annual Key West Paddle Classic
  • Sue Cooper 305-304-4259 Email Website
  • Watersports enthusiasts on paddleboards and other self-propelled watercraft can race around the continental United States’ southernmost island during the annual Key West Paddle Classic. Presented by Lazy Dog Adventures, the 12-mile challenge takes competitors past island landmarks such as the Southernmost Point marker, Fort Zachary Taylor Historic State Park and Mallory Square, site of Key West’s nightly sunset celebration.

  • October 01 - October 01 Key West
  • Second Annual Key West Barbershop Music Fest
  • Email
  • Enjoy the uniquely American style of close acapella harmony. The Miamians of South Florida, formed in 1948, won the international championship in 1965. Afterward, the Barbershop Harmony Society was formed and today there are chapters around the world, with men and women singing and competing. Performance begins at 7 p.m., at Key West United Methodist Church, 600 Eaton St. The Miamians barbershop chorus shows benefit local charities. Tickets are $30 at the door.

  • October 06 - October 08 Key West
  • Comedy Key West Presents: Billy Anderson
  • Website
  • Hosted by Tom Dustin (Comedy Central, Winner of the Great Canadian Laugh-Off), Comedy Key West presents Billy Anderson. He can be heard on Audible’s “Sounds Like America” hosted by Jackie Kashian and seen on season 3 of the syndicated program “Laughs” on Fox television. Show starts at 8:30 p.m. Comedy Key West is located at 218 Whitehead St.


  • October 10 - October 12 Islamorada
  • Islamorada All-Tackle Bonefish and Permit Championship
  • Email Website
  • Dubbed the “Fall All-Tackle,” the three-day challenge attracts energized newcomers to face seasoned veterans in a competition that has taken place since 1970. One angler per boat pairs with a licensed captain to vie for division winners’ trophies for the three longest bonefish and three longest permit. The field is limited to 25 participants.

  • October 13 - October 16 Key Largo
  • Reef Fest 2022: An Annual Celebration of Marine Conservation
  • Email Website
  • REEF Fest includes diving, snorkeling, kayak eco-tours, ocean-themed seminars, and social events. Since 2015, REEF has hosted REEF Fest each fall in the Florida Keys. Divers, snorkelers, and ocean lovers attend REEF Fest to celebrate their love of marine life and learn about the latest in conservation. Weekend schedule is to include REEF Marine Conservation Programs, dive, snorkel and kayak trips, seminars with renowned ocean experts and more.

  • October 13 - October 27 Key West
  • “Bum Farto - The Musical”
  • Website
  • Pasión Project presents “Bum Farto -The Musical,” a hilarious true crime musical that tells the tale of an infamous fire chief who tempted fate and federal agents who set him up in a 1975 Key West drug sting known as Operation Conch. The smokin’ hot show opens at the San Carlos Institute Theater in Old Town, Key West on Thursday, October 13 through October 27. Throw on your best bellbottoms, platforms, and polyester for a sizzling 70s Opening Night Gala featuring pre-show cocktails, hors d’oeuvres, and groovy tunes to benefit the Key West Firehouse Museum. Tickets start at $35 online.

  • October 13 - October 15 Key West
  • Legends of Music Row Music Festival
  • Website
  • Book your tickets for this extraordinary three-night event, including an option for a VIP experience with an exclusive, up-close-and-personal concert setting featuring songwriting legends in country music. A musical experience like no other, Legends of Music Row is to be hosted by Country Music Hall of Fame songwriter Dean Dillon.

  • October 19 - October 19 Key West
  • Comedy Key West Presents: The Royal Roast of DJ Sanaris
  • Website
  • It's hard to say something negative about the ever-positive, smiling DJ Sanaris, but this dais will find a way. Hosted by Roast Master Landon Bradbury along with other local comedians and notable Key West celebrities. A DJ Sanaris for King event. Complimentary nibbles provided by Little Whitehouse Subs & Layla's Gather & Nourish. Doors open at 7:00 p.m., show starts at 8:00 p.m. Comedy Key West is located at 218 Whitehead St.

  • October 20 - October 22 Key West
  • Comedy Key West Presents: Dean Napolitano
  • Website
  • Comedian Dean Napolitano is a throwback to the great comedians of yesteryear with a modern twist that makes him one of the most prevalent comedians working today. A true storyteller with imaginative delivery that makes audiences feel as if they have been through each experience themselves.Doors open at 7:30 p.m., show starts at 8:30 p.m. Comedy Key West is located at 218 Whitehead St.

  • October 21 - October 30 Key West
  • Key West Fantasy Fest
  • Website
  • This outrageous 10-day costuming and masking celebration features dozens of masquerade competitions, themed parties and other exuberant events. The 2022 theme is ‘Cult Classics and Cartoon Chaos!' Check the website for the full schedule and more details.

  • October 21 - October 22 Key West
  • Bahama Village Goombay Festival
  • Website
  • 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.

  • October 22 - October 22 Key West
  • Smallest Parade in the Universe
  • Website
  • Everyone’s favorite miniature parade returns! Artists compete for cash prizes and bragging rights with pint-sized floats to suit this year’s Fantasy Fest theme: Cult Classics and Cartoon Chaos! The fantastical entries are on view all month before being auctioned Oct 22 at 7 p.m., at The Studios of Key West, and 533 Eaton St., with proceeds to benefit MARC House.

  • October 23 - October 23 Key West
  • Zombie Bike Ride
  • Website
  • 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. when Zombie Land opens, at Fort East Martello Museum, a reputedly haunted historic site overlooking the Atlantic Ocean at 3501 S. Roosevelt Blvd. Live music, entertainment and face painting. Register for $5 per person.

  • October 24 - October 24 Key West
  • Heroes and Villains 5k Run/Walk
  • Beth Moyes 305-747-8563 Email Website
  • Be super, be evil, be awesome and get your run on! Dress up as your favorite Superhero or Super Villain and run, walk or fly to the finish line. Prizes are awarded for most creative, best group, scariest and funniest characters. Winner medals and awards are to given for overall male and female winners, masters (40+) male and female winners. Register online. Race starts at 6 p.m. The race begins and ends at Southernmost Beach Café.

  • October 25 - October 28 Key West
  • Key West Burlesque presents: Burlesquers Stripfinity War
  • Website
  • In a different dimension of the multiverse, the salacious stripping superhero's known as the Burlesquers must enlist the help of the Garters of the Galaxy to collect and protect the stones at all cost in this bawdy burlesque parody featuring all of your favorite Key West Burlesque and celebrity out of town guests. Tickets and showtimes available online; doors open 7 p.m., show starts 8 p.m. at Key West Theater, 512 Eaton St.

  • October 26 - October 26 Key West
  • Pet Masquerade
  • Website
  • This year’s carousel of frisky pets and playful owners perform for fame, fortune and prizes onstage at Key West Amphitheater, at Truman Waterfront Park. Starts 6:30 p.m. Proceeds benefit the Lower Keys Friends of Animals; free to watch.

  • October 27 - October 27 Key West
  • 39th Annual Key West Headdress Ball
  • Website
  • Talented headdress makers compete for first- through third-place prizes. The popular event returns to the Coffee Butler Amphitheater, Truman Waterfront Park. Doors open to the outdoor gala around 6:30 p.m., show starts 8 p.m. Sponsored by the Key West Business Guild. Tickets for purchase online.

  • October 28 - October 28 Key West
  • Masquerade March
  • Website
  • Costumed merrymakers parade through Old Town. Begins at Old Town Wine & Spirits, Truman Avenue at 5:30 pm; free to join the crowd as they parade through Old Town with music and noisemakers.

  • October 28 - October 29 Islamorada
  • Fall Backcountry Fly Championship Series
  • Website
  • Tournament anglers are to compete to catch the most inches of snook and redfish on fly in a challenge where 1 inch equals 1 point. Awards are to be given to the grand champion, the anglers who catch the largest snook and redfish and the “King of the Backcountry” series grand champion, among others.

  • October 29 - October 29 Key West
  • Bud Light Fantasy Fest Parade
  • Website
  • Lavishly decorated floats, costumed characters, bands and elaborately garbed marching groups are to make a splash on Key West's Duval Street. The glittering parade is the traditional highlight of the annual Fantasy Fest masking and costuming celebration. Parade steps off at 7 p.m. Floats, bands and other parade participants traditionally travel down Whitehead toward the Gulf of Mexico, turn onto Front Street and then proceed the mile down Duval to the Atlantic Ocean.

  • October 29 - October 29 Key West
  • Key West Woman's Club Parade Viewing Dinner Party
  • RSVP 305-294-2039 Email
  • Experience exceptional viewing of an extraordinary parade as it rolls down Duval Street. A costumed theme is “Betty Boop” and a three-course VIP exclusive catered dinner is to be served. Priority seats remain; make reservations early. Red carpet treatment is $275 per person. The Key West Woman’s Club, a volunteer service organization, is housed in a building that is one of the few privately owned mansions remaining on historic Duval Street. Proceeds are to benefit its continued restoration.

  • October 29 - October 29 Key Largo
  • Underwater Pumpkin Carving Contest
  • 305-451-3595 Website
  • Scuba divers can participate in a fun-filled buddy challenge to create the most unique Jack O'Lantern underwater during both dives of the afternoon charter! The contest will be held in the Florida Keys National Marine Sanctuary and the Amoray Diver crew will judge the entries. Dive purchase includes a two-tank dive trip, a cleaned pumpkin ready for carving, tanks and weights. Check in to Amoray Dive Center, mile marker 104.2, at 12:30 p.m. Bring your favorite carving utensils and creative ideas! Prizes awarded to the top three carved pumpkins.

  • October 30 - October 30 Key West
  • Rams Head presents The Wallflowers
  • Box Office 305-985-0433 Email Website
  • For the past 30 years, the Jakob Dylan-led act has stood as one of rock’s most dynamic and purposeful bands – a unit dedicated to and continually honing a sound that meshes timeless songwriting and storytelling with a hard-hitting and decidedly modern musical attack. Does open 7 p.m., show starts 8 p.m. at Key West Theater, 512 Eaton St.


  • November 05 - November 05 Marathon
  • Stone Crab Claw Eating Contest
  • Website
  • In this unique contest, amateur eaters age 18 and over compete to crack and consume 25 stone crab claws, picking them clean, in the fastest time. If a tie occurs, a 10-claw tiebreaker will be held to determine the winner. The much-anticipated event is to begin at 1p.m., staged at Keys Fisheries Market and Marina, located off U.S. Highway 1 on Marathon’s 35th Street gulfside. Contestants must register by noon. Stone crab season runs from Oct. 15 to May 1.

  • November 06 - November 13 Key West
  • Race World Offshore World Championship
  • Website
  • Racing teams and fans are to gather in Key West for an amazing Offshore World Championship experience. RWO is the premier Offshore Racing Sanctioning body in the United States and is dedicated to producing an unforgettable week. With the most experienced team in all of offshore racing around the world, RWO anticipates another spectacular event.

  • November 10 - November 12 Big Pine Key
  • Sugarloaf Showdown
  • Email Website
  • Presented by the Lower Keys Guides Association, the tournament raises money for the Florida Keys Guides Trust Foundation. The foundation provides funds to assist fishing guides who are recovering from an illness or injury. Participants must use either spin or fly tackle to pursue the catch-and-release tournament’s target species of bonefish, permit and barracuda. A maximum of three fish of each species can be scored per team per day.

  • November 10 - November 13 Key West
  • Green Fairy Fest
  • Website
  • An official Raceworld Offshore event, enjoy grand tastings, silent auction, concerts, sunset sails, performers, cocktail competitions, tastings and much more. Events are to be headquartered at Stock Island's Absinthe House.

  • November 12 - November 12 Islamorada
  • MOTE's Ocean Fest
  • Website
  • Underwater and outdoor enthusiasts, ecotravelers and families are encouraged to celebrate the marine environment! From 10 a.m. to 4 p.m., enjoy a day of fun, crafts, games, music, food and shopping during the outdoor community celebration of the oceans at Founders Park's green lawn and amphitheater. Attendees can explore conservation and environmental exhibits, meet live animals and experience touch tanks, view and purchase wares from local marine artists and vendors, enjoy music and try their skill at active amusements. Meet Mote scientists along with other conservation and environmental organizations.

  • November 12 - November 12 Key Largo
  • Garden Club of the Upper Keys Fall Festival
  • Website
  • Save the date! A special event is planned to commemorate the Garden Club of the Upper Keys 70th anniversary. The GCUK is a not-for-profit organization dedicated to promoting, developing and conserving the natural beauty of the Florida Keys. More details to be announced.

  • November 12 - November 12 Islamorada
  • Smuggler's Night at the Museum
  • Website
  • Boogie over to the Florida Keys History & Discovery Center's signature annual fundraising event, themed to tie into the museum’s fall lecture Series, “Smuggling in the Florida Keys.” Travel back to a boisterous time of bell bottoms and platform shoes. Your evening begins with a wine tasting. Use your souvenir glass and enjoy hors d’oeuvres while sampling quality wines and spirits. Then, be transported to an elegant dinner, dancing and dessert under the stars on the oceanside patio. You will also find great deals at the extensive live, silent and online auctions. Tickets $200 per person, available online. The event takes place from 6-10 p.m. at the museum, which is located at the Islander Resort, mile marker 82.1.

  • November 13 - November 13 Key Largo
  • First State Bank Key Largo Bridge Run
  • Website
  • Runners from around the U.S. and other countries can challenge their best times amid spectacular scenery during this Half Marathon &5k Run/Walk weekend event over the beautiful Jewfish Creek Bridge at the top of the Florida Keys Overseas Highway, overlooking the Key Largo Bay. Sunday's race starts and finishes at Gilbert's Resort. The course is USATF certified.

  • November 17 - November 19 Islamorada
  • Cheeca Lodge & Spa All-American Backcountry Tournament
  • Website
  • Anglers compete for prizes and trophies in this annual event targeting snook, redfish, bonefish, tarpon and permit. The tournament was inspired by the 41st U.S. President George H. W. Bush and honors war heroes in the esteemed competition held over Veteran’s Day weekend. Proceeds benefit the Guides Trust Foundation.

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