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Events in Key West

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

Events in Key West for 2021

  • September 15 - Nov 30, 2021 Key West
  • Scarecrows in the Forest Art Exhibit and Contest
  • Website
  • The Key West Tropical Forest & Botanical Garden is to showcase local artists’, community members’ and local students’ unique versions of the fall season’s ‘Scarecrows in the Tropical Forest.’ Made from natural and recycled materials, the exhibit, open 10 a.m. to 4 p.m. daily, will be a lesson in recycling, art talent and a contest with cash prizes for the entries. The Garden is located at 5210 College Road.

  • October 07 - 28, 2021 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: All-A Daze for a Holiday! The fantastical entries are on view all month before being auctioned Oct 23 at 7 p.m., at The Studios of Key West, and 533 Eaton St., with proceeds to benefit MARC House.


  • October 22 - 31, 2021 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 2021 theme is 'All a Daze for a Holiday!' Check the website for the full schedule and more details.

  • October 26 Key West
  • Key West Burlesque presents: Harry Potter and the Enchanted Tassle, A Parody
  • Website
  • Ready your wands and study your spells! It's time to enter the wizarding world of Harriet Potter and the Enchanted Tassel: A Burlesque Parody. Whether you're Gryffindor, Ravenclaw, Hufflepuff, or Slytherin, this enthralling show is sure to have you on the edge of your Nimbus 2000 as you join Auntie Harriet Potter on a salacious search for a magical missing tassel. Doors open 7PM, show starts 8PM at Key West Theater, 512 Eaton St.

  • November 03 Key West
  • The Studios of Key West presents: The Mon Valley Medium
  • Website
  • Alec Silberblatt’s one-person play tells the story of Mack, a yinzer (meaning he grew up and lives in the Mon Valley of Western PA) who always believed in ghosts. But after the local medium proves himself to be a fraud, Mack is left questioning what is true and what is perception. In his darkly comic tale, Silberblatt takes the audience through one man’s involvement in a vigilante killing, and into an investigation of why we believe what we believe. Held in the The Studios of Key West Courtyard at 529 Eaton St. Show starts 6:30 p.m. Tickets available online. Seating is limited.

  • November 07 Key West
  • Mike Nash & Southern Drawl Band
  • Website
  • With story teller songs about life and love, lyrical tales from the unique people he's met along the way, and of course plenty of summertime "drinkin' at the lake tunes" with an island-inspired twist, there's something in a Mike Nash show for everyone to relate to. Doors open 6 p.m.; show starts 7 p.m. at Key West Theater, 512 Eaton St.

  • November 07 - 14, 2021 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 09 - 11, 2021 Key West
  • Bum Farto: The Musical
  • Website
  • Based on a true and crazy Key West story, this show features an exceptional cast of 18 singers, dancers and actors performing 14 song and dance numbers in styles ranging from salsa to Carolina Shag and even includes a tap dancing ‘Square Fish’!  Show starts 8 p.m. at Key West Theater, 512 Eaton St.

  • November 14 Key West
  • Montessori United 5k & Kids' Fun Run
  • Website
  • Walk, run or stroll this 5K/1m/.5m to support Montessori education in Key West! Finisher medals given to all participants, t-shirts to the first 150 to register. Award medals for the 5K and 1mile races! Starts at 8 a.m., Higgs Beach. Register online. Proceeds benefit May Sands Montessori School & the Montessori Children's School.

  • November 17 - 21, 2021 Key West
  • Key West Film Festival
  • Website
  • Showcasing films that exhibit excellence in storytelling, the festival's lineup is to feature special events, as well as screenings at Tropic Cinema, 416 Eaton St. 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. KWFF strives to showcase the best of Florida filmmaking talent, while highlighting visiting filmmakers and industry leaders through discussions and workshops, with access to some of the biggest names in the film business. The festival also looks to support the next generation of local student filmmakers with scholarships and other key awards.

  • November 19 Key West
  • Rams Head presents: John Fogerty at Coffee Butler Amphitheater
  • Website
  • John Fogerty is a true American treasure. As leader of Creedence Clearwater Revival, Fogerty forged a distinctive, groundbreaking sound all his own, equal parts blues, country, pop, rockabilly, R&B, swamp boogie, and Southern fried rock ‘n’ roll, all united by his uniquely evocative lyrical perspective. Fogerty is to play his Creedence Clearwater Revival hits & more. Tickets online. Doors open 5:30 p.m., show starts 7 p.m.

  • December 03 - 05, 2021 Key West
  • COAST is CLEAR Music and Arts Festival
  • Website
  • Enjoy a weekend in the sun surrounded by close compadres — or simply folks you’ve only just met because of a shared love of music and art. The festival's main event is an all-day concert Saturday. VIP and General Admission tickets still available, at $225 pp and $105, respectively. Festival is to be held rain or shine, at Fort East Martello, 3501 S. Roosevelt Blvd.

  • December 04 Key West
  • Key West Triathlon, Sprint & Olympic Triathlon
  • Email Website
  • Athletes will converge on the southernmost island on the United States and enjoy a break from the ordinary. Staged at Higgs Beach, athletes will enjoy a warm Atlantic Ocean swim in full view of spectators.  The bike course is set against along US1 by Smather’s Beach. The Olympic distance athletes will have two loops on the course, while the sprint distance will do so once. The run also consists of a scenic view along Smather’s Beach. Friends, family and music welcome the athletes through the finish line. 

  • December 11 Key West
  • Eighth Annual Florida Keys SPCA Parade of Paws
  • Website
  • Join the Florida Keys SPCA at the Higgs Beach Dog Park from 10 a.m. - 2 p.m. for a family-friendly, fun-filled day of live music, local vendors at the Holiday Bazaar and the crowning of the 2021 Royal Court.  Enjoy pictures with Santa, sloppy kisses at the Kiss A Bull booth, fun raffles and a dog parade where all pups are welcome to strut their stuff around the beach!  Costumes encouraged!  All proceeds from the event will benefit the homeless animals of the Middle and Lower Keys.

  • December 11 Key West
  • Rams Head presents: The Temptations at Coffee Butler Amphitheater
  • Website
  • The Temptations, often referred to as “American Music Royalty,” are world-renowned superstars of entertainment, revered for their phenomenal catalog of music, and prolific career. Otis Williams, the sole surviving original Temptation, Ron Tyson, a lead vocalist with the group for 37 years, Terry Weeks, a lead vocalist for 23 years, and Willie Greene, Jr., base vocalist with the group for four years, are still serenading fans with their soulful voices, lighting up stages with their famous Temptations’ Walk, and bringing joy to audiences of all ages. Doors open 5:30 p.m., show starts 7 p.m.

  • December 12 Key West
  • The Kingston Trio at Key West Theater
  • Website
  • All three current members, Mike Marvin, Tim Gorelangton and Don Marovich, have intrinsic links to and experience with the original group: Mike is the adopted son of founding member Nick Reynolds, who was also his musical mentor; Tim, a close friend since boyhood, is one of the few musicians outside the Trio who has recorded with Nick Reynolds; and Don Marovich, who has performed with the Trio and who plays the guitar, banjo and mandolin. Many of their personal memories recall the iconic trio’s performances and journey as folk music made its extraordinary ascent to the pinnacle of popular culture – and the top of the music charts. Doors open 7 p.m., show starts 8 p.m. at Key West Theater, 512 Eaton St.