Key West Labor Day Weekend 2026
When: September 3 - September 7, 2026
Where: Key West, Duval St, Key West, FL 33040
Key West celebrates Labor Day Weekend September 3–7, 2026, with five days of concerts, street parties, food events, races, waterfront activities and celebrations across the island. The holiday weekend is anchored by the Just a Few Friends celebration honoring Jimmy Buffett's Key West legacy, with major events taking place from Duval Street to Truman Waterfront Park.
Thursday opens with activities around the island and the Cheeseburger Beach Battle at Southernmost Beach Resort. Friday brings a free Duval Street Party featuring Gary & the Landsharks, recreating the spirit of the legendary 1998 Parrot Head street party. Saturday includes the Parrots & Margaritas 5K, waterfront activities, live music and sunset celebrations.
Sunday, September 6, is one of the biggest days of the weekend. The 7th Annual BBQ Rib Battle takes over Ann Street during the day before the Second Line Memorial Walking Parade begins at 5:00 PM. The procession heads toward Truman Waterfront Park, where the free Party in the Park: Tribute to Bubba runs from 6:00 PM to 10:00 PM. The weekend continues through Labor Day Monday with sailing adventures, pool parties, live music and a final evening celebration.
Visitors can use KeyWestTourist.com's Labor Day Weekend planner to follow the weekend day by day, discover individual events and find things to do between the major celebrations, including snorkeling, sunset sails, sandbar trips, watersports, fishing and Key West live music.
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