There is always something fun to do in Key West. This calendar of events is frequently updated.
Key West’s Most Complete Calendar of Events.
This calendar of events for Key West includes nearly every happening on the island throughout the year. Something missing? If you know of any Key West calendar events that we have overlooked please let us know by filling out this short form and we’ll quickly add it. Check back frequently: more events, dates, and details are added as the season progresses.
If you have an event you would like to add to our calendar, visit this page to submit your event details: https://www.keywesttravelguide.com/submit-your-event-for-the-key-west-calendar/
April 2026 Key West Calendar of Events
Spring is in full swing in April. Between the legendary Conch Republic Independence Celebration and the world-class 7-Mile Bridge Run, the island is buzzing with energy and unique island traditions.
Festivals & Uniquely Key West
Date(s): April 17 – 26, 2026
Category: Festival / Uniquely Key West
A 10-day celebration of Key West’s “secession” from the U.S. Highlights include the Drag Race on Duval (high heels, not cars), the World’s Longest Parade, and the Great Sea Battle in the harbor.Visit Website →
Date(s): Saturday, April 11, 2026
Category: Festivities / Sports
One of the most scenic running events in the world. 1,500 runners traverse the historic bridge over open water. Note: The bridge closes temporarily for the race, so plan travel accordingly!Visit Website →
Date(s): Starts April 29, 2026
Category: Festival / Music
The end of April marks the beginning of this massive musical event, bringing the best Nashville and local talent to stages across the island.Visit Website →
Culture & Arts
Date(s): Friday, April 3, 2026 (6:00 PM – 9:00 PM)
Category: Arts / Culture
Explore the galleries, boutiques, and bookshops of the “Fabulous 500 Block” of Fleming Street with live music and refreshments.
Date(s): Thursday, April 16, 2026 (6:00 PM – 9:00 PM)
Category: Arts & Culture
A monthly celebration of the White Street Gallery District featuring new exhibitions and artist receptions.Visit Website →
Fishing & Tournaments
Date(s): Ongoing throughout April
Category: Tournament
April is prime time for Tarpon and Permit. This tournament is open to all skill levels and covers offshore, reef, and flats fishing.Visit Website →
LGBTQ Events
Date(s): Saturday, April 18, 2026 (Part of Independence Celebration)
Category: LGBTQ / Uniquely Key West
The world-famous drag queen sprint down Duval Street in high heels. It’s one of the most photographed and hilarious events of the year.Visit Website →
Holidays & Festivities
- April 5: Easter Sunday – Many locals and visitors attend the Easter Sunrise Service at Higgs Beach. Check local listings for waterfront brunch specials.
- April 22: Earth Day – Eco-tours and beach cleanups hosted by the Key West Sea Turtle Club and Reef Relief.
May 2026 Key West Calendar of Events
May is a spectacular time in the Keys, blending the high energy of the Songwriters Festival with the relaxed kickoff of the summer season. Here is your guide to the best events on the island this month.
Festivals & Uniquely Key West
Date(s): April 29 – May 3, 2026
Category: Festival / Music
The largest festival of its kind in the world, featuring over 200 performers and 50+ shows at various island venues, from intimate bars to large outdoor stages.Visit Website →
Date(s): Sunday, May 24, 2026
Category: Uniquely Key West
A hilarious local tradition where participants build boats out of a single sheet of plywood, duct tape, and a 2×4, then attempt to race them in the Bight.Visit Website →
Performances & Culture
Date(s): Saturday, May 9, 2026
Category: Performance
Rock icons performing live at the Key West Theater with special guests The Marshall Tucker Band.Visit Website →
Date(s): Thursday, May 21, 2026 (6:00 PM – 9:00 PM)
Category: Arts & Culture
A long-standing tradition on the 3rd Thursday of the month, where the White Street Gallery District opens its doors for exhibitions and receptions.Visit Website →
Fishing & Tournaments
Date(s): Ongoing throughout May
Category: Tournament
An 8-month-long tournament open to all anglers. Entries can be weighed at various Key West marinas to win prizes in multiple categories.Visit Website →
LGBTQ Events
Date(s): Saturday, May 30, 2026 (7:30 PM)
Category: LGBTQ / Festivities
The official variety show kickoff for Key West Pride Week. A local tradition of talent, drag, and comedy at the Key West Theater.Visit Website →
Holidays & Festivities
- May 5: Cinco de Mayo – Island-wide taco and tequila specials at Amigos Tortilla Bar and Sandbar Key West.
- May 10: Mother’s Day – Waterfront brunches at Hot Tin Roof and Latitudes.
- May 23–25: Memorial Day Weekend – The unofficial start of summer with ceremonies at the Bayview Park veteran memorials and beach festivities.
If you know of any Key West calendar events that we have overlooked please let us know by filling out this short form and we’ll quickly add it. And check back frequently – since more dates and details will be added as the season progresses.