38th Anniversary Hemingway 5K Sunset Run & Paddleboard Race
When: July 24 - July 25, 2027
Where: Southernmost Beach Cafe, 1405 Duval St, Key West, FL 33040
The 38th Anniversary Hemingway 5K Sunset Run & Paddleboard Race returns to Key West during Hemingway Days 2027, bringing together runners, walkers, paddleboarders, and spectators for one of the island's most anticipated annual traditions. Held at the Southernmost Beach Café, the weekend combines friendly competition with the laid-back atmosphere that has made Hemingway Days famous.
The signature Hemingway 5K Sunset Run takes participants on a scenic course through the historic streets of Old Town Key West as the sun begins to set. The flat, fast route welcomes experienced runners chasing a personal best along with walkers, families, and visitors who simply want to enjoy one of the island's most memorable races.
The weekend also features the popular Paddleboard Race, where competitors paddle the waters off Key West before returning to the beach for awards and festivities. Together, the two events celebrate Ernest Hemingway's adventurous spirit and the island's unique connection to outdoor recreation and the sea.
Following the races, participants and spectators gather for the traditional beach celebration at Southernmost Beach Café, featuring awards, refreshments, live entertainment, local vendors, and plenty of opportunities to relax with fellow competitors while enjoying the oceanfront setting.
Whether you're participating or cheering from the shoreline, the Hemingway 5K Weekend offers an unforgettable way to experience one of Key West's signature festivals. Registration is available in advance, and early sign-up is recommended as the event attracts competitors from across Florida and around the country.
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