Hemingway Sunset Run 5K
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Hemingway 5K Sunset Run & Paddleboard Race
The Hemingway 5K Sunset Run is part of the Hemingway Days weekend in Key West and is presented as the event’s 38th anniversary edition. The event includes a 5K run/walk through Old Town and waterfront areas of Key West, a paddleboard race, and related activities across the weekend of July 24–25, 2027, within the larger Hemingway Days dates of July 21–25, 2027.
Race operations use the area around the Southernmost Beach Cafe at 1405 Duval Street for registration and the awards/beach party, while the 5K start area is near the corner of Whitehead and United close to the original Southernmost Buoy. The awards/beach party features tastings of Papa’s Pilar Rum and Islamorada Beer, raffles, and live entertainment; the cafe will have extended happy hour and select menu specials for participants.
A separate Beach N’ Beer Mile takes place on the beach at Southernmost Beach Cafe; it is a one mile course run as four loops with four beer tickets and a custom shirt included. That event is not timed, has a $55 entry listed, and awards prizes for Best Team Spirit, Best Dressed, and Least Dressed. Paddleboard racers are required to have a Personal Flotation Device during the race and paddleboard rental options are listed by the organizers. A pool party at Blue Flamingo Resort is scheduled as part of the weekend activities. Visit the organization's website for the most recent information.
