Hemingway Sunset Run 5K
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Hemingway 5K Sunset Run
The Hemingway 5K Sunset Run is part of a weekend of events in Key West tied to Hemingway Days in July 2026. The event marks the 37th anniversary and combines a road 5K run/walk with a paddleboard race along Key West’s Old Town and waterfront areas. Registration and post-race activities are centered at Southernmost Beach Cafe, 1405 Duval Street, where an awards and beach party includes tastings of Papa’s Pilar Rum and Islamorada Beer, snacks, raffles, live entertainment, and extended venue specials for participants.
The weekend also includes a Beach N’ Beer Mile held on the beach at Southernmost Beach Cafe. That event covers four loops with four beer tastings from Islamorada Beer Co., includes a custom shirt, is not timed, and carries a listed entry fee. Costume participants can compete for prizes in categories such as Best Team Spirit, Best Dressed, and Least Dressed. A pool party is scheduled at The Backyard Pool and Social Club at Blue Flamingo Resort.
A paddleboard race runs alongside the on-land events. Participants are required to have a personal flotation device during the paddleboard race. Paddleboard rental and purchase options are listed, including local outfitters and a retail discount for participants who show proof of race registration. The event features a 2026 race shirt and medal. Visit the organization's website for the most recent information.
