33rd Annual Hemingway 5K Sunset Run/Walk and Paddleboard Race, Presented by Papa’s Pilar Rum

33rd Annual Hemingway 5K Sunset Run/Walk

and Paddleboard Race, Presented by Papa’s Pilar Rum,

 Set for July 23, 2022

KEY WEST, Florida Keys — Old Town Key West will host runners, fitness walkers and paddleboard enthusiasts testing their skills and celebrating Ernest Hemingway’s sporting lifestyle on Saturday evening, July 23rd. The longest on-going race in Key West, the Hemingway 5K Sunset Run/Walk and Paddleboard Race, presented by Papa’s Pilar Rum, was rated in 2018 #3 on Active.com’s list of top ten international destination races to turn into a vacation.

The well-established athletic challenges are part of Hemingway Days, a six-day commemoration of the life and work of the author who lived and wrote in Key West for most of the 1930s.

“This is the hottest race in Key West! Literally!” said organizer Barbara Wright. “It’s held on a hot summer night here, but the great thing is participants can jump in the beautiful Key West waters to cool off after the race and there are lots of cold libations to satisfy your thirst!”

The Paddleboard Race will kick off at 5:30 p.m. at the island city’s Southernmost Beach, 1405 Duval St. on the Atlantic Ocean. A 3-mile ocean course will challenge paddlers before they finish back at the beach.

Then, at 7:30 p.m., the popular 5K Run/Walk will begin at the Southernmost Point in the continental United States, oceanfront at Whitehead and South streets. Participants race through picturesque Old Town Key West, past landmarks including the Ernest Hemingway Home & Museum, Green Parrot Bar, the Key West Lighthouse, and Custom House as they complete the fast, flat 3.1-mile course.

On race day, a registration booth will be open from 3:00-7:00 p.m. on the beach outside of the Southernmost Beach Café. Race packets, bibs and shirts can be picked up there. Collectible race tech shirts feature iconic Key West images and more.

Afterwards, a great post-race awards beach party with live music is scheduled outside in the same area and includes free food, libations, and raffles.

A fun pub crawl is planned for Sunday from noon-3:00. The “Smile Mile” includes several bars offering a free adult beverage. The fee includes drinks, souvenir and last stop party at Rams Head Southernmost on Whitehead Street. Crawlers can sign up on RunSignUp.com and need to stop by the Smile Mile table at Registration on Saturday to pick up materials.

Paddleboard awards will be presented to the first- through third-place male and female finishers, plus to the top first- through third-place male and female race boards. In the 5K, awards await the top three male and female overall finishers, top three male and female masters, and top two male and female finishers in ten-year age categories ranging from 9 and under to 75 and over. For walkers, awards will be given to the top three male and female finishers. Great prizes, including Caribbean trips, will go to the overall winners!

In addition, those competing in all challenges will receive unique finisher medals.

For those who want a triple challenge, they can join the Annual Hemingway Bicycle Tour, which starts at 9 a.m. on race day at Sombrero Beach. To register, visit keywesthalfmarathon.com/Hemingway-event-details/.

Fuel up at Sea, Key West’s free Pre-Race Power Brunch on race day from 11 a.m.-2 p.m. at 720B Caroline St. In addition to brunch, the locally owned watersports equipment store is offering all race participants a 20% discount on any store purchases!

Runners and paddleboarders can register online at RunSignUp.com or download registration forms by visiting keywesthalfmarathon.com.

The entry fee includes a collectible race tech shirt, chip timing, custom bibs, food, finisher medals, libations and lots of great giveaways including Caribbean Resort Trips for up to four!

Proceeds benefit Key West Sunrise Rotary Scholarship Fund and the College of the Florida Keys Youth Swim Program. Sponsored in part by Monroe County Tourist Development Council, Papa’s Pilar Rum, Southernmost Beach Resort, Lazy Dog Key West, and Elite Caribbean Island Resorts, and includes prizes from many great Key West establishments, including Sunshine Scooters! 

More information: Barb Wright (305) 240-0727 or visit keywesthalfmarathon.com.


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