There is never a shortage of activity on Key West. A new year is here and the events keep on coming. Culinary delights start off the year here in the Keys; with events like the Seafood Festival and the Food and Wine Festival foodies are in heaven! There are also many marathons and other physical events like flag football and SUP for those athletic types. And let’s not forget about the art scene; concerts, art openings, seminars and plays are abundant throughout the year, starting off with the Annual Literary Seminar in January. So no matter when you visit our island Paradise, you will find as much action and entertainment or relaxation as you are looking for.
April 2025
Mote’s Ocean Fest Special Event – April 12, 2025 – 10:00 AM - 3:00 PM@ Truman Waterfront ParkMote Marine Lab’s Ocean Fest is a free, family friendly event with live music, food trucks, a kid zone, and artisan and non-profit vendors in Truman Waterfront Park.
The Great Egg Hunt & Migration Mania – April 12, 2025 – 10:00 AM - 2:00 PM@ The Key West Tropical Forest & Botanical Gardens on College Road.
43rd Annual Conch Republic Days – April 18, 2025 – April 25, 2025 – Over 20 events across the island will celebrate Key West’s “independence” from the US. The festival will be a family-fun event held in historic and unique venues, waterfront parks, saloons at sea, and a reenactment of the Great Battle of the Conch Republic.
Conch Republic Independence Celebration – Street Fair Special Event – April 19, 2025 – 10:00 AM - 6:00 PM@ Duval Street. This is a street closure for Duval Street. Duval will be closed between Eaton and Greene Streets.
Conch Republic Independence Celebration – Drag Race Special Event – April 19, 2025 – 2:00 PM - 6:00 PM@ Duval Street. This is a street closure for the 700 Block of Duval Street. Duval will be closed between Angela and Petronia.
Key West Artisan Market – April 20, 2025 – At the Key West Wildlife Center, 1801 White Street, from 10am until 2pm. Local artisans include culinary, textile, jewelry, wood, artists and crafters, curiosities, a Local Author’s Nook, a live variety show, fresh produce, and lots of great, fresh food. Each week, the theme is different, focused on island living and local charities. Guests are encouraged to go green and ride bikes. There is ample free parking and marked handicapped spots at the park. Please BYOB (bring your own bags).
Earth Day – April 22, 2025 – 8:00 AM - 4:00 PM@ Sonny McCoy Indigenous Park.
Conch Republic Independence Celebration – World’s Looooogest Parade Special Event – April 24, 2025 – 8:00 PM - 9:00 PM@ Duval StreetThis is a street closure. Duval Street will be closed between South and Greene Streets. Greene Street will be closed between Duval and Elizabeth. United will be closed between Simonton & Whitehead for floats & vehicles to lineup. Parade begins at United & Duval, goes to Greene St., turns right on Greene to Elizabeth to Lazy Way Lane.
Conch Republic Independence Celebration – Great Sea Battle of the CR – LAND FORCES at Mallory Square Special Event – April 25, 2025 – 6:00 PM - 8:00 PM@ Mallory Square.
Key West Literary Seminar: Elizabeth Bishop – April 25, 2025 – Join Arlo Haskell, Executive Director of Key West Literary Seminar; Ronald Patkus, Head of Special Collections and College Historian at Vassar College; and curators Jonathan Ellis of the University of Sheffield and Susan Rosenbaum of the University of Georgia, for a conversation in the Bishop Garden about the exhibition, composed of 55 postcards drawn from Vassar’s collection of more than 500. 624 White Street from 5:30 – 7:30pm.
Mariner’s March 5K Special Event – April 26, 2025 – 6:00 AM - 11:00 AM. This race will primarily be run on the sidewalks, KWPD will assist intersections and as the runners need to enter the street. Traffic may be delayed on Truman Avenue between Simonton and Windsor from 7:50-8:05am and 9-9:20am.
Blessing of the Animals Special Event – April 26, 2025 – 8:30 AM - 10:30 AM@ Sonny McCoy Indigenous park. This event is held in the parking lot of the Sonny McCoy Indigenous Park.
Conch Republic Independence Celebration – Julie Hanson Memorial Bed Races Special Event – April 26, 2025 – 12:00 PM - 6:30 PM@ Duval StreetThis is a street closure for Duval Street between Olivia and Southard.
Conch Republic Independence Celebration – Brawl on Duval Special Event – April 26, 2025 – 3:00 PM - 11:00 PM@ Duval Street. This is a street closure. Duval Street will be closed between Front & Caroline. Greene Street will be closed between Simonton & Whitehead.
Reelin for the Cause Kids Fishing Tournament Special Event – April 26, 2025 – 3:00 PM - 8:30 PM@ Edward B. Knight Pier. The Pier will be closed from approximately 3:00 PM to 9:00 PM for a Kids Fishing Tournament.
Movies Under the Stars at the Tropic Cinema Special Event – April 26, 2025 – 5:00 PM - 10:30 PM. This is a street closure. Eaton St. will be closed between Duval St. and Whitehead St.Join us outside the Tropic each month for a free outdoor screening of a cinema classic! Concessions will be available inside the Tropic lobby; limited seating will be provided but you’re welcome to bring chairs or blankets. All screenings start approximately 1/2 hour after sunset. No need to purchase tickets, just show up and enjoy! SPACEBALLS!
Key West Artisan Market – April 27, 2025 – At the Key West Wildlife Center, 1801 White Street, from 10am until 2pm. Local artisans include culinary, textile, jewelry, wood, artists and crafters, curiosities, a Local Author’s Nook, a live variety show, fresh produce, and lots of great, fresh food. Each week, the theme is different, focused on island living and local charities. Guests are encouraged to go green and ride bikes. There is ample free parking and marked handicapped spots at the park. Please BYOB (bring your own bags).
Sheriff’s Farm Open House – April 27, 2025 – The farm is open to the public on the second and fourth Sundays of each month from 1 to 3 pm. It’s FREE and donations are always appreciated! 5501 College Rd., Key West, FL, 33040 from 1 – 3pm.
29th Annual Key West Songwriter’s Festival – April 30, 2025 – May 4, 2025 – The Key West Songwriters Festival is the largest festival of its kind in the world. It spans five days and nights, during which time songwriters introduce crowds to the faces, voices, and stories behind the songs.
May 2025
Key West Songwriter’s Festival Free Concert Special Event – May 3, 2025 – 7:00 PM - 10:00 PM@ Duval Street. This is a street closure. The 100 & 200 blocks of Duval Street and Greene Street between Fitzpatrick & Ann Streets will be closed from 6:00 AM to Midnight. Concert begins at 7:00 PM.
Run for Rhonda Special Event – May 4, 2025 – 7:00 AM - 11:00 AM@ Truman Waterfront Park. There is no street closure. Setup begins at 5:00 AM, race begins at 7:00 AM. Racers do 2 laps around the promenade.
Key West Outdoor Movies – May 9, 2025 – Key West Outdoor Movies presents a family-friendly film (to be named) at the parade grounds at Fort East Martello, 3501 S. Roosevelt Blvd. The grounds open at 5 p.m. with free admission. Food and drink will be available for sale by vendors onsite, and there will be free popcorn and activities for all. Bring low chairs or a blanket. The movie starts at dusk. This is the season finale for Outdoor Movie Night.
Sheriff’s Farm Open House – May 11, 2025 – The farm is open to the public on the second and fourth Sundays of each month from 1 to 3 pm. It’s FREE and donations are always appreciated! 5501 College Rd., Key West, FL, 33040 from 1 – 3pm.
Walk on White – May 15, 2025 – 6 – 9pm, Walk on White is a monthly art walk in the White Street Gallery District of Key West, Florida. It has been held on the third Thursday of each month since 1999 and features over 25 local businesses. Walk on White is a great opportunity to explore the local art scene in Key West. You can find a variety of art, from paintings and sculptures to jewelry and pottery. There is something for everyone at Walk on White. Enjoy complimentary libations at participating businesses during Walk on White. This is a great way to relax and enjoy the art while meeting other art lovers. Walk on White often features special events, such as live music, artist talks, and workshops. These events are a great way to learn more about the local art scene and meet the artists.
Menendez Miler 5K Walk/Run Special Event – May 24, 2025 – 6:00 AM - 11:00 AM@ Truman Waterfront Park. No street closures. Setup 6am, race begins at 8am. 3 loops around Truman Waterfront Park, beginning and ending near the Coast Guard Ingham Museum.
Sheriff’s Farm Open House – May 25, 2025 – The farm is open to the public on the second and fourth Sundays of each month from 1 to 3 pm. It’s FREE and donations are always appreciated! 5501 College Rd., Key West, FL, 33040 from 1 – 3pm.
June 2025
Summer Solstice Celebration at Mallory Square – June 1, 2025 – June 20, 2025 – Every evening in Key West, locals and visitors gather at the waterfront Mallory Square for the world-famous Sunset Celebration, to enjoy the unique gathering of skilled artisans, exciting performers, and local vendors — and to toast the setting of the sun. Beginning June 1, a colorful series of special events and performances will take place nightly from 7 p.m. until after sunset, leading up to the June 20 Summer Solstice, the official first day of summer.
Sheriff’s Farm Open House – June 8, 2025 – The farm is open to the public on the second and fourth Sundays of each month from 1 to 3 pm. It’s FREE and donations are always appreciated! 5501 College Rd., Key West, FL, 33040 from 1 – 3pm.
Key West Gator Club Dolphin Derby – June 13, 2025 – June 15, 2025 – Anglers targeting dolphin fish can compete for $15 thousand in guaranteed cash prizes during the Key West Gator Club Dolphin Derby June 13 through 15. Tournament location to be announced. The team weighing in the heaviest dolphin fish takes home a grand prize of $5 thousand. Proceeds benefit scholarships for Key West High School graduates attending University of Florida.
College of the Florida Keys Swim Around Key West – June 14, 2025 – Embark on an adventurous competitive swim – a 12.5 loop around the island. The pristine waters around Key West give swimmers great views of both the land and underwater life. Compete in different categories including solo swimmer, solo swimmers with fins, solo swimmers using a mermaid tail or a monofin, or gather your friends and compete in the relay category of 2-person, 3-person, 4-person, 5-person or 6-person teams. Not interested in the full island swim? Try some of the smaller races offered, a 6.1-mile swim, a 2-mile swim, a 1-mile swim or an 800-yard swim. Swims begin and end at Higgs Beach, 1000 Atlantic Boulevard.
VFW Fishing Tournament – June 20, 2025 – June 22, 2025 – VFW’s annual fishing tournament returns with over $75,000 in cash and prizes. The big change for 2025 will be that all registered boats are able to fish two days, with no separate registration required for each fishing day. Tournament events are held at the VFW post at 2200 N. Roosevelt Blvd.
Sheriff’s Farm Open House – June 22, 2025 – The farm is open to the public on the second and fourth Sundays of each month from 1 to 3 pm. It’s FREE and donations are always appreciated! 5501 College Rd., Key West, FL, 33040 from 1 – 3pm.
Key West Pride – June 22, 2025 – June 29, 2025 – Celebrate Pride on the tropical island of Key West that is legendary for its laid-back style and its open and accepting atmosphere. This year’s event theme is “Still Rising,” honoring the history of the LGBTQ+ community. Along with Key West Art & Historical Society and the Stonewall National Museum, a special exhibit will showcase “50 Years: The Stonewall Uprising.” This year’s Pride also features late-night dance parties, historical tours of Gay Key West, daytime and sunset sailing excursions, a private beach party, pool parties, film screenings, drag performances, comedy night, a bar crawl by trolley and much more.
Key West Pride Street Fair and Dance Party Special Event – June 28, 2025 – 7:00 AM - 11:00 PM@ Duval Street. This is a street closure. The 700-900 blocks of Duval will be closed from 7am – 11pm. Setup is from 7am – 3pm. The Street Fair and Dance Party is from 4-11pm.
Key West Pride Parade Special Event – June 29, 2025 – 7:00 PM - 8:30 PM@ Duval Street. This is a street closure. Participants line up at Truman Waterfront Park, head North on Whitehead St. to Duval, to United St.
July 2025
The Key Lime Festival – July 2, 2025 to July 6, 2025 – Welcome to the Key Lime Festival: America’s Favorite Citrus Celebration! In the Florida Keys we like to celebrate the things that make our islands unique. Citrus, eccentrics, people & pie. Our celebrations are fun, odd & unforgettable. Our people are too. Come on down to the birthplace of Key Lime Pie for a little taste and you’ll see what we mean. Love & Limes!
Rotary Club of Key West July 4th Celebration Special Event – July 4, 2025 – 4:00 PM - 10:00 PM@ Edward B. Knight Pier. This is a street closure. White Street will be closed from 5:00 PM – 10:00 PM between Casa Marina Court and Laird Street. The Sonny McCoy Indigenous Park Parking Lot will be closed from 4:00 PM to 10:00 PM for a fundraiser with food and drinks. The Edward B. Knight Pier will be closed.
Studios of Key West 4th of July Rooftop Fireworks Viewing – July 4, 2025 – Join Studios of Key West for a special Independence Day party on the Hugh’s View rooftop! Ticket price includes a free drink, a view of the fireworks on the horizon, and a DJ keeping the soundtrack flowing until 10pm. Wear your red, white and bluest finery and bring your firecracker personality.
Key West Marlin Tournament – July 16, 2025 – July 23, 2025 – Ernest Hemingway look-alikes, writers, anglers, and fans of the late author’s work are to gather in Key West for the annual Hemingway Days celebration. The festival honors the legacy of the American literary giant who lived and wrote on the island for most of the 1930s. Events include the legendary Hemingway Look-Alike Contest, the wacky Running of the Bulls on Sat. July 26, literary presentations, a commemoration of the 126th anniversary of Hemingway’s July 21 birth, a museum exhibit, a marlin tournament, a 5k run and paddleboard race, a street fair and more.
Hemingway Days – July 22, 2025 – July 27, 2025 – Ernest Hemingway look-alikes, writers, anglers, and fans of the late author’s work are to gather in Key West for the annual Hemingway Days celebration. The festival honors the legacy of the American literary giant who lived and wrote on the island for most of the 1930s. Events include the legendary Hemingway Look-Alike Contest, the wacky Running of the Bulls on Sat. July 26, literary presentations, a commemoration of the 126th anniversary of Hemingway’s July 21 birth, a museum exhibit, a marlin tournament, a 5k run and paddleboard race, a street fair and more.
Sloppy Joe’s Look-Alike Contest – July 23, 2025 – July 27, 2025 – 9:00 AM - 11:00 PM. This is a street closure. Greene Street will be closed between Duval St. and Ann St. The look-alike challenge is a highlight of Key West’s July 23-27 Hemingway Days celebration, created to salute the writing talent and adventurous life of the literary master who lived and wrote in Key West throughout the 1930s. It takes place at Sloppy Joe’s Bar, 201 Duval St., where Hemingway enjoyed sharing cocktails and camaraderie with friends while living in Key West in the 1930s. The contest’s preliminary rounds are set for 6:30 p.m. Thursday and Friday, July 24 and 25, and the newest “Papa” is to be chosen during a final round beginning at 6:30 p.m. Saturday, July 26.
Running of the Bulls Special Event – July 26, 2025 – A festival tradition, this wacky event is sponsored by Sloppy Joe’s Bar and features Hemingway Look-Alike Contest winners and entrants dressed in their Pamplona best — and a breed of “bull” found only in Key West. The fun starts on Greene Street outside Sloppy Joe’s at 1 p.m. Free for spectators.
Hemingway 5K – July 26, 2025 – July 27, 2025 – Join fellow runners and walkers for the 36th annual Hemingway 5k Sunset Run. This year, final registration for the evening race is at Southernmost Beach Cafe, 1405 Duval St., but, new for 2025, the race is to start and end at the Southernmost Point Buoy/Marker. The run is followed by a beach party with awards and tastings of Papa’s Pilar Rum and Islamorada Brewery & Distillery Beer, plus raffles and live entertainment. On Sunday, The Beach N’ Beer Mile departs from Southernmost Beach Cafe at 12 p.m., including 4 beers. Costumes are encouraged! A pool party follows at Rum Row, 3824 N. Roosevelt, from 3 to 6 p.m.
Brightwild and Ramshead Presents the 2nd Annual Mini Music Fest – July 30, 2025 – August 3, 2025 – Mini Music Fest, where Florida’s Mini Lobster Season meets the vibrant sounds of Nashville! Hosted by Brightwild and Rams Head Presents Key West, this event promises an unforgettable experience.
Reef Relief 10th Annual Jerry Garcia Birthday Bash – July 31, 2025 – Reef Relief and the Green Parrot 10th Annual Jerry Garcia Birthday Bash with Live Music, Silent Auction, Raffles and more!
August 2025
Key West Tropical Heat – August 13, 2025 – August 17, 2025 – Enjoy five days of sizzling happenings in the island city whose openness and respect for diversity have made it a world-renowned gay vacation destination. The festival’s events range from all-male theme parties, pool parties and entertainment showcases at the island’s LGBTQ venues. Attendees can also enjoy activities ranging from eco-tours to museum explorations.
Rum Fest Key West – August 13, 2025 – August 17, 2025 – Key West is famous for tropical heat, mouth watering seafood and some of the best rum you can get your hands on, among many other things. Rum Fest Key West showcases the best rum from around the world. Experiences include sunset sails, sandbar trips, rum strolls, food and cigar events featuring rum, two Jesse Rice concerts and a third concert with Cliff Cody and Sharese during the annual rum cake competition at Key West Theater, a rum grand tasting and more.
Just a Few Friends, Key West Special Event – August 31, 2025 – 4:00 PM - 10:00 PM@ Duval Street. This is a street closure. Parade begins in the 100 block of Duval, down Duval St., right on Southard St. to Truman Waterfront Park.
September 2025
Womenfest Key West – September 3, 2025- September 7, 2025 – The popular festival for lesbians and their friends is designed to allow singles, couples and groups of women to experience the atmosphere of openness and acceptance that has made Key West an internationally acclaimed lesbian and gay vacation destination. Activities range from beach parties, snorkeling, sunset cruises to live entertainment, an art workshop and much more.
October 2025
Southernmost Half Marathon Special Event – October 12, 2025 – 6:00 AM - 10:00 AM. This is a rolling street closure. The race begins and ends at Higgs Beach. The route consists of Higgs Beach to Fort Street, through Truman Waterfront Park, up Front Street to Mallory Square then reversing back to Higgs Beach.
Fantasy Fest – October 17, 2025 – 26, 2025 – Fantasy Fest is an annual 10-day party in paradise for grown-ups. Started in 1979 by a small group of Key West locals, the party was created to bring visitors to the island in what was a typically quiet, but beautiful season. It worked. Fantasy Fest has grown every year since its inception and is now the wildest extravaganza around! Fun-loving revelers from around the globe bring their creativity and imaginations as they descend upon Key West each year in October for 10 days filled with costuming, parades, libations, and excitement! The winning theme for Key West Fantasy Fest 2025, which is scheduled for Oct. 17-26, is “Bedtime Stories & Magical Monsters.” Ellen LaMoia of Key West, Fla., has scored Fantasy Fest Parade Grand Stand seats where she will enjoy the 2025 spectacle seated among the parade’s judges and organizers for her contribution to the theme.
Fantasy Fest Zombie Bike Ride – October 19, 2025 – The annual Rock n’ Roll costumed Zombie bike ride returns for another wild run on Sunday, Oct. 19. The Zombieland pre-ride party takes place at Fort East Martello, 3501 S. Roosevelt, from 2 to 6 p.m. with face and body painters, food vendors and a full bar. The ride, with thousands of costumed zombies, rolls out at 6 p.m. going down A-1-A then through downtown. The ride ends with a dance party at the Coffee Butler Amphitheater at Truman Waterfront Park presented by Rams Head. Register online in advance for $10.
Fantasy Fest Masquerade March (aka The Local’s Parade) – October 24, 2025 – Join the hugely popular Fantasy Fest tradition known as the locals’ parade that highlights costumes, creativity and community. The Captain Morgan Masquerade March is a grown-up moving cocktail and dance party that begins at 5:30 p.m. at Truman Ave. and Frances St. The route winds its way north to Fleming St., stopping at participating guest houses that hand out complimentary beverages.
Fantasy Fest Parade – October 25, 2025 – Join 70,000 exuberant partygoers as the Key West Fantasy Fest parade rolls down Duval Street featuring glittering floats, spectacular costumes and dazzling dancing groups, some dressed and decorated to illuminate this year’s theme of “Bedtime Stories & Magical Monsters.” It doesn’t get any wilder than this! Parade steps off at 7 PM; Free to attend for spectators
November 2025
December 2025
More About Key West
For more information about the fun side of Key West, things to do and see in our island city, go to our Key West Web Site. And, remember to check out our restaurant reviews as you surely must eat while down here!
Island Genn – Key West Concierge
