Key West Events & Festivals
Key West has a peculiar talent for turning almost anything into a festival. Seafood? Festival. Key lime pie? Festival. Hemingway? Naturally. Fast boats? Absolutely. Costumes and body paint? Now we're getting somewhere.
Here are some of the biggest annual events worth putting on your calendar.
🏃 Key West Half Marathon & Runfest | January 15–17, 2027
One of Key West's biggest winter sporting weekends brings runners through Old Town and along the waterfront. The 2027 weekend includes the 5K, 8K, 10K and Half Marathon, along with the decidedly Key West Hemingway Rum Stroll and Beach N' Beer Mile.
Official Key West Half Marathon & Runfest
🎸 Mile 0 Fest | January 26–30, 2027
Five days of Red Dirt, Americana and Texas Country music turn Key West into one enormous music venue. The Coffee Butler Amphitheater hosts the big evening shows, while performances and parties spill into bars, beaches, resorts, boats and other venues around the island. The 2027 edition marks the festival's 10th anniversary.
🍷 Key West Food & Wine Festival | January 27–31, 2027
Five days devoted to the finer side of island life: chef dinners, wine tastings, culinary experiences and special events around Key West. The 2027 festival is themed “Connected by the Oceans” and explores food and wine traditions from five continents.
Official Key West Food & Wine Festival
🦞 Florida Keys Seafood Festival | February 13–14, 2027
This one belongs on the Tipsy list. Truman Waterfront Park fills with fresh Florida Keys seafood, live music and local vendors. Expect spiny lobster, stone crab, Key West pink shrimp, conch, smoked fish dip and other straight-from-the-Keys favorites.
Official Florida Keys Seafood Festival
🐚 Conch Republic Independence Celebration | April
Key West's wonderfully ridiculous micronation commemorates its mock secession from the United States in 1982. The celebration traditionally stretches across multiple days with parties, parades, conch-shell blowing, costumes, schooners and the famous mock sea battle in Key West Harbor. The 2026 celebration ran April 17–26; the organizer has not yet posted the full 2027 schedule.
Official Conch Republic Independence Celebration
🎶 Key West Songwriters Festival | April 28–May 2, 2027
For five days, Key West becomes one giant listening room. More than 150 songwriters typically perform everything from intimate acoustic sets and songwriter rounds to waterfront concerts and sunset performances. It's especially fun because many of the people on stage are the writers behind songs you've heard a thousand times.
Official Key West Songwriters Festival
🏳️🌈 Key West Pride | June 2–6, 2027
Key West's One Human Family philosophy gets the full rainbow treatment during Pride. Expect parties, live entertainment, sunset sails, drag performances, a street fair and the Pride Parade down Duval Street. The Key West Business Guild has already published June 2–6 as the 2027 dates.
Official Key West Pride / Key West Business Guild
🍋 Key Lime Festival | July 1–5, 2027
Only Key West could devote several days to a tiny green citrus fruit and somehow turn it into a party. The festival celebrates the birthplace of Key lime pie with tastings, cocktail events, pie competitions, dinners and plenty of wonderfully oddball activities. The festival's official site lists July 1–5 for 2027.
✍️ Hemingway Days | July
Papa returns every summer. Hemingway Days celebrates Ernest Hemingway's Key West years with literary events, fishing traditions, the Hemingway 5K and, most famously, the Hemingway Look-Alike Contest at Sloppy Joe's, when an impressive migration of white-bearded “Papas” descends upon Duval Street.
The 2027 Hemingway 5K weekend is confirmed for July 24–25, 2027, but the complete 2027 Hemingway Days festival schedule has not yet been published.
🦞 Key West Lobsterfest | August 11–15, 2027
When Florida's spiny lobster season opens, Key West celebrates appropriately: by eating a heroic quantity of lobster. Lobsterfest combines lobster dinners, parties, a pub crawl and the big Duval Street Fair and concert. The organizers have already announced August 11–15 for the 29th annual festival in 2027.
🎭 Fantasy Fest | October 16–25, 2026
And then Key West completely loses its mind.
Fantasy Fest is the island's legendary 10-day costume celebration, filling Old Town with elaborate costumes, body painting, parties, street events, the Masquerade March and the enormous Fantasy Fest Parade. The 2026 theme is “Musical Icons and Iconic Musicals.” The organizers have also already announced October 22–31, 2027 for next year's festival.
🏁 Key West Offshore World Championship | November 1–8, 2026
For one week, the soundtrack of Key West changes from steel drums to very large engines. Race World Offshore's championship brings high-performance offshore racing to the waters around Key West, with racing on November 4, 6 and 8 in 2026, plus testing, parties and the famous boat parade through town.
Race World Offshore – Key West World Championship
🎬 Key West Film Festival | November 18–22, 2026
The Key West Film Festival brings filmmakers, actors and movie lovers to the island for screenings, special events and conversations at venues throughout Key West. The 2026 festival is scheduled for November 18–22.
Official Key West Film Festival
🎄 Key West Holiday Fest | Late November–December
Christmas in Key West involves considerably fewer snow boots and considerably more palm trees. Holiday Fest traditionally runs from around Thanksgiving through December with the Harbor Walk of Lights, decorated boats, holiday markets, light displays, parties and Key West's wonderfully tropical holiday parade.
👠 Key West New Year's Eve | December 31, 2026
Key West doesn't settle for dropping one object at midnight. Around the island you'll find several celebrations, but the most famous is the Red Shoe Drop on Duval Street, where a giant red high heel descends above Bourbon Street Pub as the clock strikes midnight.