Calendar of Events

Current Key West Events

Image for Sloppy Joe’s 43rd Annual Hemingway Look-Alike Contest Image for Sloppy Joe’s 43rd Annual Hemingway Look-Alike Contest Image for Sloppy Joe’s 43rd Annual Hemingway Look-Alike Contest Image for Sloppy Joe’s 43rd Annual Hemingway Look-Alike Contest
Image for 31st Annual Dolphin Tournament Lower Keys Chamber of Commerce Image for 31st Annual Dolphin Tournament Lower Keys Chamber of Commerce Image for 31st Annual Dolphin Tournament Lower Keys Chamber of Commerce Image for 31st Annual Dolphin Tournament Lower Keys Chamber of Commerce
Image for Hemingway 5k Sunset Run & Paddleboard Race Image for Hemingway 5k Sunset Run & Paddleboard Race Image for Hemingway 5k Sunset Run & Paddleboard Race Image for Hemingway 5k Sunset Run & Paddleboard Race
Image for Key West Pride Image for Key West Pride Image for Key West Pride Image for Key West Pride
Image for Christopher Peterson's Eyecons at Birdcage Cabaret Image for Christopher Peterson's Eyecons at Birdcage Cabaret Image for Christopher Peterson's Eyecons at Birdcage Cabaret Image for Christopher Peterson's Eyecons at Birdcage Cabaret
Image for Fish & Friends Seminar Image for Fish & Friends Seminar Image for Fish & Friends Seminar Image for Fish & Friends Seminar
Image for SALVAGING THE DEEP - AN Image for SALVAGING THE DEEP - AN Image for SALVAGING THE DEEP - AN Image for SALVAGING THE DEEP - AN
Image for Key West Art & Historical Society: Flora & Fauna - Early Naturalists in Florida
  • Mar 15, 2024 - Sep 13, 2024 Key West Arts & Culture
  • Key West Art & Historical Society: Flora & Fauna - Early Naturalists in Florida
  • Website
  • Enjoy the “Flora & Fauna: Early Naturalists in Florida” exhibit through September 13 at Key West Museum of Art & History's Custom House, Museum, 281 Front Street. The exhibit includes short biographies of the principal naturalists working in the Florida Territory in the early nineteenth century alongside representations of their Florida-inspired works. Their observation of plants and animals was an art as well as a science.
Image for Waterfront Playhouse: Lost in Yonkers
  • Apr 24, 2024 - May 11, 2024 Key West Arts & Culture
  • Waterfront Playhouse: Lost in Yonkers
  • Website
  • Neil Simon's story, set in 1942 Brooklyn, of two brothers, Jay and Arty, who must learn to live with their stern Grandma, their Aunt Bella, and their Uncle Louie, a henchman for some gangsters. Showtimes at 8 p.m. with a Saturday 2 p.m. matinee on May 4. Tickets $40 to $85. 407 Wall Street at Mallory Square.
Image for Key West Tropical Forest & Botanical Garden: Art in the Garden
  • Apr 28, 2024 - Jul 31, 2024 Key West Arts & Culture
  • Key West Tropical Forest & Botanical Garden: Art in the Garden
  • Website
  • Emphasizing harmony with nature, the return of Art in the Garden showcases local art and sculptures with artistic expressions. Artworks are earth-friendly in the selection of materials and themes and include recycled, repurposed, and natural material. Meander over garden boardwalks and down pathways through dappled shade, colorful blossoms and winged creatures to spot many beautiful works of art. View daily through July 31. 5210 College Rd.
Image for 28th Annual Key West Songwriters Festival
  • May 1, 2024 - May 5, 2024 Key West Arts & Culture
  • 28th Annual Key West Songwriters Festival
  • Website
  • The Key West Songwriters Festival is the largest festival of its kind in the world. It revolves around five days and nights where live music bliss introduces crowds to the faces, voices and stories behind the songs. Performances take place at numerous theaters, bars and event spaces around Key West. The opening night headliner on Duval Street May 1 is Dylan Marlowe; Cole Swindell performs May 2 in a ticketed concert at Coffee Butler Amphitheater, and Dallas Davidson headlines a free street performance Saturday May 4 on Duval Street. For a full schedule of events, download the Key West Songwriters Festival app.
Image for Studios of Key West: First Thursday Open House
  • May 2, 2024 Key West Arts & Culture
  • Studios of Key West: First Thursday Open House
  • Website
  • During the First Thursday Open House event, the Studios keep the lights on late and throw the doors open to celebrate the newest work in its galleries. Stop in to say hello, relax with a glass of wine on the rooftop terrace, tour the third floor artist studios and see the just-installed exhibitions in the various galleries. 6 to 8 p.m. at 533 Eaton St.
Image for Coffee Butler Amphitheater: Cole Swindell
Image for Key West Outdoor Movies: Pixar's UP
  • May 3, 2024 Key West Arts & Culture
  • Key West Outdoor Movies: Pixar's UP
  • Website
  • All are welcome to this free, family-friendly Key West Outdoor Movie Night featuring Pixar's "UP" on the lawn at Fort East Martello, 3501 S. Roosevelt Blvd. Doors open at 6:30 p.m. with the movie starting at dusk. Bring a blanket or a low-profile chair. Popcorn is free.
Image for The Studios of Key West: Gallery Talk with Artist Anthony Mancuso
Image for Cow Key Bridge Run: Cow Wars 2024 - May the 4th Be With Moo!
  • May 4, 2024 Key West
  • Cow Key Bridge Run: Cow Wars 2024 - May the 4th Be With Moo!
  • Website
  • Dress up in your best bovine costume and trek across the infinitely short Cow Key Channel Bridge. Get in the MOO-d from 9 to 11 a.m. before the "race" at the Bloody MOO-ey party at the Rum Row bar at The Gates Hotel. The entire herd will move over to stage at the starting area in front of the bridge between 11 a.m. and 12 p.m. At 12 noon, the race starts with cows away! Everyone is invited back to Rum Row and the Sunset Green Lawn for an after-race party and awards ceremony. Sign-up includes a race bib. Commemorative T-shirts will be available for purchase at the pre-race party. All proceeds benefit the MCSO Animal Farm and the Highgate Foundation.
Image for Talk Derby to Me
  • May 4, 2024 Key West Arts & Culture
  • Talk Derby to Me
  • Website
  • Support the Key West Mounted Police Unit at the 7th annual "Talk Derby to Me" event at The Gardens Hotel, 526 Angela St. Dress up to compete in the best costume, best hat and best couple contests. Get photos with the Key West P.D. horses and officers, and enjoy mint juleps and food. $25 donation at the door.
Image for Schooner America 2.0: Starry Night Stargazing Sail
  • May 4, 2024 - May 5, 2024 Key West
  • Schooner America 2.0: Starry Night Stargazing Sail
  • Website
  • Sail through Key West waters by starlight on this stargazing sailing adventure aboard the 105-foot Schooner America 2.0, featuring live narration from NASA Solar System Ambassador and Key West resident, Kevin Gallagher. Trip departs at 9:15 p.m. from the dock at Key West Bight, 202 William St.
Image for Sloppy Joe's 87th Anniversary at the Corner of Duval and Greene Streets
Image for Schooner Wharf Bar: Cinco de Mayo
  • May 5, 2024 Key West
  • Schooner Wharf Bar: Cinco de Mayo
  • Website
  • Schooner Wharf Bar's 25th annual Cinco de Mayo celebration takes place from 7 p.m. until midnight. Win a prize for the best Mexican hat, compete in the Super Hot Taco Eating Contest for prizes, and party with live music by the Cool Coconuts Band. 202 William St.
Image for Run for Rhonda 5k
  • May 5, 2024 Key West
  • Run for Rhonda 5k
  • Website
  • Run or walk your way through Key West on Cinco de Mayo for the first annual Run for Rhonda. Starting and finishing at Truman Waterfront Park, the race will be followed by a fabulous post-race party with DJ Jimmy Jam, adult and non-alcoholic beverages, festive food, a raffle and more. The run honors the legacy of Key West resident Rhonda Flores and supports a college scholarship for a participant in the Take Stock in Children program.
Image for The Marker: Cinco de Mayo Margarita Battle
  • May 5, 2024 Key West
  • The Marker: Cinco de Mayo Margarita Battle
  • Website
  • Gather by the pool at The Marker, 200 William St., at 3 p.m. for the 2nd annual island-wide margarita battle. Bartenders from The Starboard Restaurant & Bar at The Marker, Southernmost Beach Cafe, The Gates Hotel and 24 North Hotel shake up their tastiest margaritas, and you get to be the judge. Live music by Les Greene and The Swayzees.
Image for Key West Art & Historical Society Distinguished Speaker Series: Key West Ghost Stories with Wayne Garcia
Image for Reef Relief Annual Luau Fundraiser
  • May 11, 2024 Key West
  • Reef Relief Annual Luau Fundraiser
  • Website
  • Reef Relief holds its annual luau celebration from 5 to 8:30 p.m. at Lagerheads Beach Bar & Grill, located at 0 Simonton St. Enjoy live music from Gary Hempsey, games, a raffle, a silent auction and more.
Image for Tennessee Williams Theatre: One Night of Queen
  • May 12, 2024 Key West LGBTQ
  • Tennessee Williams Theatre: One Night of Queen
  • Website
  • For over 20 years Gary Mullen and The Works have been performing their world-renowned "One Night of Queen" live concert. Gary Mullen & The Works will have you dancing in the aisles during their show, while the band pays tribute to the stage theatrics, showmanship, and music of Rock & Roll Hall of Fame inductees: Queen. Tickets $45 to $135. Show at 8 p.m. 5901 College Rd.
Image for Sheriff's Animal Farm Open House
  • May 12, 2024 Key West
  • Sheriff's Animal Farm Open House
  • Website
  • Visit the family-friendly Monroe County Sheriff's Animal Farm, open the second and fourth Sundays of each month from 1 to 3 p.m. Visits are free of charge, but donations are always welcomed. Stock Island Detention Center, 5501 College Rd.
Image for Studios of Key West: Craig Foster Discusses His New Book, Amphibious Soul
  • May 17, 2024 Key West Arts & Culture
  • Studios of Key West: Craig Foster Discusses His New Book, Amphibious Soul
  • Website
  • From the creator of the beloved Academy Award winning documentary “My Octopus Teacher” comes "Amphibious Soul," Craig Foster’s thrilling memoir of a life spent exploring the most incredible places on Earth – from the Great African Seaforest to the crocodile lairs of the Okavango Delta. Foster reveals how we can attend to the earthly beauty around us and deepen our love for all living things, whether we make our homes in the country, the city, or anywhere in between. $40 ticket includes a copy of the book. Doors open at 6 p.m., talk at 7 p.m.
Image for Key West Tropical Forest & Botanical Garden: Rum Infused Adult Scavenger Hunt
Image for Reelin' For the Cause Kids Fishing Tournement
  • May 18, 2024 Key West Fishing
  • Reelin' For the Cause Kids Fishing Tournement
  • Website
  • The tournament raises awareness about congenital heart defects and provides funds to support families with infants born with these disorders. Check in at 9:30 a.m. at Edward B. Knight (White Street) Pier at 9:30 a.m. $15 per child. Rod, reel and bait provided. Lines in at 10 a.m.; awards ceremony at 11:45 a.m. Awards for biggest fish in each age group: 3 to 5; 6 to 8; and 9 to 13. Sharks will be their own category with one award for the largest shark across all age groups. There is also a silent auction at the pier during the tournament.
Image for Schooner Wharf Bar: Minimal Regatta
  • May 26, 2024 Key West
  • Schooner Wharf Bar: Minimal Regatta
  • Website
  • Watch sailors make a splash in homemade vessels made from plywood and duct tape in the craziest regatta you'll ever see on the waters of Key West Bight. Watch from the Historic Seaport walkways near Schooner Wharf. 12 noon at 202 William St.
Image for Sheriff’s Animal Farm Open House
  • May 26, 2024 Key West
  • Sheriff’s Animal Farm Open House
  • Website
  • Visit the family-friendly Monroe County Sheriff's Animal Farm, open the second and fourth Sundays of each month from 1 to 3 p.m. Visits are free of charge, but donations are always welcomed. Stock Island Detention Center, 5501 College Rd.
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