The Hemingway 5k Sunset Run and Paddleboard Race: A Tribute to a Legendary Writer's Sporting Lifestyle

Set in Key West, Florida Keys, the island once home to the legendary writer Ernest Hemingway during the 1930s, the Hemingway 5k Sunset Run and Paddleboard Race are annual sporting events inspired by Hemingway's active lifestyle. Scheduled for July 22, these events promise to challenge athletes on both land and water, testing their speed and endurance.

The Hemingway Days Celebration and the 5k Sunset Run and Paddleboard Race

The 5k and paddleboard race is now in its 34th year and is presented by Papa’s Pilar Rum. This nationally acclaimed event is part of the annual Hemingway Days celebration in Key West, a tribute to the late author's life and work.

  • Registration and packet pickup for the race is scheduled from 3-7 p.m. on the day of the event, at the Southernmost Beach Resort, located at 1405 Duval St.

  • The Paddleboard Race, managed by Lazy Dog Adventures, will start at 5:30 p.m. on the Atlantic Ocean beach beside the Southernmost Beach Café, which is also at 1405 Duval St. Athletes are expected to paddle a 3-mile ocean course before finishing back at the beach.

  • The 5k Sunset Run, welcoming both runners and walkers, will begin at 7:30 p.m. at the Southernmost Point in the continental United States, overlooking the Atlantic in the 1300 block of Whitehead Street. Participants will enjoy a fast, flat 3.1-mile course that winds through part of Key West’s scenic Old Town, past landmarks such as the Ernest Hemingway Home & Museum.

Post-Race Celebrations

Following the 5k run, an awards beach party is scheduled to kick off at 8 p.m. outside the Southernmost Beach Café. The event will include entertainment, food, raffles, and libations. Awards will be given to finishers in both the paddleboard race and the 5k, spread across multiple categories. Athletes competing in both challenges will receive special medals.

Other Related Events and Registration Details

Additional events in conjunction with the 5k and paddleboard challenge include Sunday’s Hemingway Rum Bar Stroll and a fun-filled Beer Mile.

Registration for the races is available online at Virtual participation options are also offered for those unable to attend the event in person or who prefer to compete on their own terms.

The registration fee for each event is $61 per person through June 30, increasing to $63 per person after that date. Athletes registering for both challenges receive a 10% discount on their second event. Military and local discounts are also available. The entry fee includes a collectible race tech shirt, finisher medal, food, libations, and other giveaways.

Event information: