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Calendar of Events

Current Key West Events

Image for Fantasy Fest 2022 Image for Fantasy Fest 2022 Image for Fantasy Fest 2022 Image for Fantasy Fest 2022
  • Sponsored Event
  • Oct 21, 2022 - Oct 30, 2022 Key West
  • Fantasy Fest 2022
  • Website Key West
  • 305-295-9112 E-mail
  • Facebook Twitter Instagram
  • This outrageous 10-day costuming and masking celebration features flamboyant masquerade competitions, and over 30 cleverly themed Parties and performances. Togas, Tutu’s, Body Paint and Burlesque, Halo’s, and Homemade Bikinis. Join the fun!
Image for REEF Fest ~ An Annual Celebration of Marine Conservation Image for REEF Fest ~ An Annual Celebration of Marine Conservation Image for REEF Fest ~ An Annual Celebration of Marine Conservation Image for REEF Fest ~ An Annual Celebration of Marine Conservation
Image for Key West Bicentennial Exhibit at The Custom House Museum
  • Mar 31, 2022 - Dec 11, 2022 Key West Arts & Culture
  • Key West Bicentennial Exhibit at The Custom House Museum
  • Website
  • Key West Art & Historical Society welcomes the public to view the ‘Key West 200’ exhibit at the Custom House Museum, 281 Front St. The exhibit is to highlight Key West’s people, culture and community beginning with the settlers and government officials who arrived on this remote island in early 1822, featuring rarely displayed artifacts. Divided by decade, the exhibit emphasizes many of the significant moments and people that have influenced so much of what we celebrate today.
Image for ‘Kids Free Florida Keys’
  • Sep 6, 2022 - Oct 16, 2022 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.
Image for Comedy Key West Presents: Billy Anderson
  • Oct 6, 2022 - Oct 8, 2022 Key West Arts & Culture
  • 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.
Image for “Bum Farto - The Musical”
  • Oct 13, 2022 - Oct 27, 2022 Key West Arts & Culture
  • “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.
Image for Legends of Music Row Music Festival
  • Oct 13, 2022 - Oct 15, 2022 Key West Arts & Culture
  • 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.
Image for Native Plant Sale at the Key West Tropical Forest & Botanical Garden
  • Oct 15, 2022 Key West Environmental
  • Native Plant Sale at the Key West Tropical Forest & Botanical Garden
  • Website
  • The plant nursery offers native trees, shrubs, vegetables and vines for sale from 9 a.m. to noon the third Saturday of the month.  Master Gardener volunteers will be on site to help answer any plant questions. There are 165 species of plants available with an inventory totaling more than 2,000 plants that attract birds and butterflies in 1-gallon to 10-gallon pots. Key West Botanical Garden members receive a discount. The Garden, located at 5210 College Road on Stock Island, is a 501 (c) 3 non-profit corporation and all proceeds directly benefit the Garden’s conservation program.
Image for Comedy Key West Presents: The Royal Roast of DJ Sanaris
  • Oct 19, 2022 Key West Arts & Culture
  • 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.
Image for Comedy Key West Presents: Dean Napolitano
  • Oct 20, 2022 - Oct 22, 2022 Key West Arts & Culture
  • 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.
Image for Bahama Village Goombay Festival
  • Oct 21, 2022 - Oct 22, 2022 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.
Image for Key West Fantasy Fest
  • Oct 21, 2022 - Oct 30, 2022 Key West LGBTQ
  • 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.
Image for Smallest Parade in the Universe
  • Oct 22, 2022 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.
Image for Zombie Bike Ride
  • Oct 23, 2022 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.
  • Oct 24, 2022 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.
Image for Key West Burlesque presents: Burlesquers Stripfinity War
  • Oct 25, 2022 - Oct 28, 2022 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.
Image for Pet Masquerade
  • Oct 26, 2022 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.
Image for 39th Annual Key West Headdress Ball
  • Oct 27, 2022 Key West LGBTQ
  • 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.
Image for Masquerade March
  • Oct 28, 2022 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.
Image for Bud Light Fantasy Fest Parade
  • Oct 29, 2022 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.
Image for Key West Woman's Club Parade Viewing Dinner Party
  • Oct 29, 2022 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.
Image for Rams Head presents The Wallflowers
  • Oct 30, 2022 Key West Arts & Culture
  • 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.
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