2026 JAFF SCHEDULE Preliminary schedule — subject to change All information / data courtesy of the event organizers. Please visit their link for tickets and updates where applicable. (Information subject to changes and errors and omissions.) Full schedule & tickets on sale May 1 April 28 for package holders April 30 for badge holders WEDNESDAY, […]
October 1 – 5, 2026 · Grand Tasting: Saturday, October 3, 3–8pm Southernmost Beach Resort, 1319 Duval Street, and venues across the island Key West oktoBREWfest is an island-wide beer festival hosted by the Key West Sunrise Rotary of the Conch Republic and the Southernmost Beach Resort. It's a fully nonprofit event, with proceeds going […]
October 15 – 23, 2026 Waterfront Playhouse, Mallory Square, 407 Wall Street The Waterfront Playhouse opens its season with an encore presentation of Hedwig and the Angry Inch, staged as a live concert event. The Obie Award–winning rock musical has a book by John Cameron Mitchell and music and lyrics by Stephen Trask. It premiered […]
October 16 - 25, 2026 2026 Theme: Musical Icons & Iconic Musicals 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. […]
Key West Headdress Ball Thursday, October 22, 2026 · Coffee Butler Amphitheater at Truman Waterfront Park Doors 6:30pm · Show 8:00pm The Key West Business Guild presents the 43rd Anniversary Headdress Ball, one of the most anticipated nights of Fantasy Fest. Legendary Key West entertainer Randy Roberts returns as host, with music by WEOW's RudeGirl. […]
45th Annual Key West Offshore World Championship November 1–8, 2026 · Truman Waterfront Park, Key West The 45th Annual XINSURANCE Key West World Championship runs Sunday, November 1 through Sunday, November 8, 2026, at Truman Waterfront Park. It's the season finale of the Race World Offshore calendar and the oldest continuously run event on the […]
November 12 – 14, 2026 Waterfront Playhouse, Mallory Square, 407 Wall Street The Waterfront Playhouse launches its Spotlight Series with the Florida premiere of , a solo play written by Jason Odell Williams. It runs about 75 minutes and takes the form of a private tour of Michelangelo's David at the Galleria dell'Accademia in Florence, […]
Sunday, November 22, 2026 Key West Theater, 512 Eaton Street The Buena Vista Orchestra comes to the Key West Theater, billed by its presenter as the world's foremost Cuban music repertory ensemble. The group works with a revolving lineup drawn from the original Buena Vista Social Club performances and from the bands of Celia Cruz, […]
December 2 – 17, 2026 Waterfront Playhouse, Mallory Square, 407 Wall Street The Waterfront Playhouse's holiday show turns the theatre into a 1940s radio studio for It's a Wonderful Life: A Live Radio Play, Joe Landry's adaptation of the Frank Capra film. A small cast plays every role, performing the story live at microphones the […]
December 8, 2026 – January 2, 2027 · Shows at 7:00pm Red Barn Theatre, 319 Duval Street (rear) The Red Barn opens its holiday slot with Shooting Star, a two-hander by Steven Dietz, one of the most widely produced playwrights working in American theater. The setup is simple enough to describe in a sentence: two […]
January 7 – 9, 2027 Waterfront Playhouse, Mallory Square, 407 Wall Street The Spotlight Series continues with Blanche and Beyond, Steve Lawson's one-man play assembled from Tennessee Williams's own letters. It's the sequel to Lawson's A Distant Country Called Youth, which drew on the early correspondence; this one covers 1945 through 1957, the stretch that […]
29th Annual Key West Half Marathon & Runfest® January 13–18, 2027 · Race weekend January 15–17 Key West offers a multitude of exciting experiences, from its diverse restaurants and vibrant nightlife to the numerous museums and art galleries. The wide range of water sports options adds an extra layer of adventure, making it an unforgettable […]
