Calendar of Events

Current Key West Events

Image for Big Pine & Lower Keys Nautical Expo Image for Big Pine & Lower Keys Nautical Expo Image for Big Pine & Lower Keys Nautical Expo Image for Big Pine & Lower Keys Nautical Expo
Image for NAS Key West Southernmost Air Spectacular Image for NAS Key West Southernmost Air Spectacular Image for NAS Key West Southernmost Air Spectacular Image for NAS Key West Southernmost Air Spectacular
Image for 18th Annual Sombrero Beach Run Image for 18th Annual Sombrero Beach Run Image for 18th Annual Sombrero Beach Run Image for 18th Annual Sombrero Beach Run
Image for Truman Waterfront Farmers Market - Every Thursday
  • Sep 19, 2024 - Sep 25, 2025 Key West
  • Truman Waterfront Farmers Market - Every Thursday
  • Website
  • Shop with a view every Thursday from 2 to 7 p.m. at the Truman Waterfront Farmers Market located on the harbor by the USCG Ingham Museum. Find great food options including ready-to-eat items, fresh Florida produce and other grocery items, along with gifts, home decor, art and more. Located at the corner of Southard Street and Weech Way.
Image for Key West Art & Historical Society: Collecting Key West - The Works of Mario Sanchez
  • Dec 6, 2024 - May 18, 2025 Key West Arts & Culture
  • Key West Art & Historical Society: Collecting Key West - The Works of Mario Sanchez
  • Website
  • Mario Sanchez (1908-2005), a Key West native, is among this country’s finest and most-recognized folk artists. In hundreds of intricately painted wood carvings created in a lifelong labor of love, Sanchez has provided a better history of Key West in the first part of the 20th century than any annals or academic texts. His bas-relief carvings, or intaglios, are a visual feast filled with the music, smells and passion of Gato’s Village, the Cuban-American community of Key West where Sanchez spent much of his life. In the carvings, each person, chicken, dog and fish has its own singular expression, attitude and identity. The exhibit is on display at the Custom House Museum daily from 10 a.m. to 5 p.m. 281 Front St.
Image for Studios of Key West: Jeffrey Cardenas - On the Reef
  • Jan 2, 2025 - Jan 30, 2025 Key West Arts & Culture
  • Studios of Key West: Jeffrey Cardenas - On the Reef
  • Website
  • Key West resident Jeffrey Cardenas has traveled from Polynesia to the Mediterranean and Caribbean Sea, photographing vibrant coral reef ecosystems. His work reveals the beauty and essential role of coral reefs in supporting diverse marine life, prompting reflection on their significance and the urgent need for their conservation. 533 Eaton St.
Image for Key West Library Speaker Series: Mondays at 6 p.m.
  • Jan 13, 2025 - Jan 27, 2025 Key West Arts & Culture
  • Key West Library Speaker Series: Mondays at 6 p.m.
  • Website
  • Authors in the Key West Library Speakers series appear on Mondays, January through March. January's featured speakers are: January 13: Ayana Mathis, author of The Unsettled (Knopf, 2023), named a New York Times and Washington Post Notable Book of 2023. January 20: Jimin Han, author of The Apology, named best book of the summer by the Los Angeles Times, Vanity Fair and others. January 27: Cathy Salustri in conversation with David Sloan - Salute is author of Florida Spectacular: Extraordinary Places and Exceptional Lives. Free to attend and no registration required. Talks take place in the library's Palm Garden, 700 Fleming St. at 6 p.m.
Image for Fringe Theater: I Love You, You're Perfect, Now Change
Image for The Southernmost Regatta
  • Jan 20, 2025 - Jan 25, 2025 Key West
  • The Southernmost Regatta
  • Website
  • Top sailing teams from around the world compete in the azure waters off Key West, showcasing colorful sails and avid sportsmanship during five consecutive days of racing. Competition is open to One Design and ORC Racing / Cruising Keelboats. Spectators can watch the races from various waterfront venues, mingle with sailors and view sailboats at the Galleon Resort's marina, 617 Front Street, after each day’s races.
Image for Kelly McGillis Classic International Flag Football Championship
  • Jan 21, 2025 - Jan 27, 2025 Key West LGBTQ
  • Kelly McGillis Classic International Flag Football Championship
  • Website
  • Women from countries far and wide will be descending upon Key West for the 32nd annual flag football competition with teams participating from USA, Morocco, Spain, Mexico, Sweden, Pakistan, Mexico, Honduras and El Salvador. Kelly McGillis will serve as grand Marshall for the players' parade from the historic seaport down Duval Street on Thursday, Jan. 25. Game activities throughout the weekend Jan. 26-28 are free for the public to attend at Wicker Field Sports Complex on Kennedy Drive off Flagler Ave.
Image for Mile 0 Fest
  • Jan 21, 2025 - Jan 25, 2025 Key West Arts & Culture
  • Mile 0 Fest
  • Website
  • Mile 0 Festival is a premier music festival that celebrates Red Dirt and Americana music. Artists includes the Red Clay Strays, Randy Rogers Band, Shane Smith & the Saints, Steve Earle, Reckless Kelly, Kaitlin Butts and many more. A variety of passes that include lodging are available along with event-only passes.
Image for Waterfront Playhouse: The Angel Next Door
  • Jan 22, 2025 - Feb 8, 2025 Key West Arts & Culture
  • Waterfront Playhouse: The Angel Next Door
  • Website
  • The wonderfully funny script by Paul Slade Smith captures the joy and wit of 1940s screwball comedies. Brace yourself for what a critic called "a perfect storm of comedic chaos, irresistible charm and rapid-fire banter." Showtimes 8 p.m. plus a 2 p.m. matinee on Feb. 1. 407 Wall St. at Mallory Square.
Image for Key West Theater: Melissa Etheridge
  • Jan 22, 2025 Key West Arts & Culture
  • Key West Theater: Melissa Etheridge
  • Website
  • Don't miss the legendary Melissa Etheridge on the Key West stop of her 2025 tour. Known for her confessional lyrics and raspy, smoky vocals, Etheridge has remained one of America’s favorite female singer-songwriters for more than two decades. Doors at 7 p.m.; show at 8 p.m. 512 Eaton Street.
Image for Key West Theater: Jon McLaughlin & Eric Hutchinson
Image for Old Island Restoration Foundation: January Home Tours
  • Jan 24, 2025 - Jan 25, 2025 Key West Arts & Culture
  • Old Island Restoration Foundation: January Home Tours
  • Website
  • Key West is home to what is considered the largest predominantly wooden historic district in the United States. One weekend a month, from January through March, five distinctive homes and their gardens open, revealing a range of architectural gems, eclectic art, transformed cigar-makers cottages, shipbuilders’ craft, re-imagined Victorian mansions, and the stories behind the facades. Home tour tickets provide entry to 5 homes at your self-guided pace during the Friday-Saturday tour dates. All tickets for sale online. Your receipt will be your ticket to enter the home. If you prefer to have a physical ticket, you can pick one up at the Oldest House Museum gift shop, 322 Duval St., the week before the tour date.
Image for Tropic Cinema: Movies Under the Stars - War Games
  • Jan 25, 2025 Key West Arts & Culture
  • Tropic Cinema: Movies Under the Stars - War Games
  • Website
  • Don't miss the monthly free Movies Under the Stars screening - this month, the movie is War Games. The film will be presented free for all, outdoors on Eaton Street. Bring chairs or blankets for seating. Concessions are to be available in the theater lobby. The film begins at approximately 6:30 p.m. 416 Eaton St.
Image for Tropic Cinema: Movies Under the Stars - War Games
  • Jan 25, 2025 Key West Arts & Culture
  • Tropic Cinema: Movies Under the Stars - War Games
  • Website
  • Don't miss the monthly free Movies Under the Stars screening - this month, the movie is War Games. The film will be presented free for all, outdoors on Eaton Street. Bring chairs or blankets for seating. Concessions are to be available in the theater lobby. The film begins a half hour after sunset. 416 Eaton St.
Image for Key West Cemetery Tour
  • Jan 26, 2025 Key West Arts & Culture
  • Key West Cemetery Tour
  • Historic Florida Keys Foundation 305-304-1453 E-mail Website
  • Historic Florida Keys Foundation holds its first Key West Cemetery tours of the season on Sunday, Jan. 26 at 9:30, 9:50 and 10:10 a.m. Groups of visitors will be escorted to the grave sites of Juana Borrero Pierra, William Curry, George Adderly, May Douglas, Hilda Russel and the USS Maine Monument. The 90-minute tour will cover about one mile - wear comfortable shoes. A donation of $20 to the foundation is appreciated. Reservations are required. Email hfkf@bellsouth.net or call 305-304-1453.
Image for Impromptu Classical Concerts: Simone Porter
  • Jan 26, 2025 Key West Arts & Culture
  • Impromptu Classical Concerts: Simone Porter
  • Website
  • Violinist Simone Porter has been recognized as an emerging artist of impassioned energy, interpretive integrity, and vibrant communication. In the past few years, she has debuted with the New York Philharmonic, the Philadelphia Orchestra, and the Los Angeles Philharmonic. Born in 1996, Simone made her professional solo debut at age 10 with the Seattle Symphony and her international debut with the Royal Philharmonic Orchestra in London at age 13. 4 p.m. at St. Paul's, 401 Duval St.
Image for Sheriff's Animal Farm Open House
  • Jan 26, 2025 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. Animals include a capybara, possum, sloths, goats, birds and many more. Visits are free of charge, but donations of cash or fresh produce are always welcomed. Stock Island Detention Center, 5501 College Rd.
Image for Red Barn Theatre: Ms Holmes & Ms Watson, Apt. 2B
Image for Key West Theater: Ben Harrison
  • Jan 29, 2025 Key West Arts & Culture
  • Key West Theater: Ben Harrison
  • Website
  • Ben Harrison is a playwright, lyricist and composer who is also an entertainer. What makes his live performances so enjoyable is that, at his core, he is a barroom guitar player/singer/songwriter who somehow manages to blend history, musical theater, Key West and humor into unusual stories that are mostly true. Key West Theater's Backstage Listening Room. Doors at 6 p.m.; show at 7 p.m. 512 Eaton Street.
Image for Coffee Butler Amphitheater: Chicago
  • Jan 31, 2025 Key West Arts & Culture
  • Coffee Butler Amphitheater: Chicago
  • Website
  • Hailed as one of the most important bands in music since the dawn of the rock and roll era, the legendary rock and roll band with horns, Chicago, came in as the highest charting American band in Billboard Magazine's Top 125 Artists Of All Time. And, Chicago is the first American rock band to chart Top 40 albums in six consecutive decades. Doors open at 6:30 p.m.; show at 8 p.m. 21 Quay Rd.
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