Hemingway Days Festival

When former Key West resident Michael Whalton conceived Hemingway Days more than 40 years ago, he couldn’t possibly foresee it would become a continuing, internationally recognized celebration of the island’s best-known inhabitant.

At the time, he was a day manager at Sloppy Joe’s Bar, famed as a hangout of Ernest Hemingway’s when he lived in 1930s Key West.

Whalton directed the festival for 16 years before moving to West Virginia in the Mid-1990s. In July 2023, he traveled back to Key West to experience Hemingway Days for the first time since his departure. During his visit, he reflected on the iconic event’s origin, growth and continued significance - particularly meaningful as the 2024 festival celebrates Ernest Hemingway’s 125th birthday.

Schedule:

1:00pm: Papa Hemingway Look-Alike Fish-Off. Cheer your favorites as the Papas & Wannabes compete in this dockside catch-and-release challenge using traditional “Cuban Yo-Yos” at Conch Republic Seafood Company docks, 631 Greene Street. Free to watch. (Silent Auction benefiting the HLAS Scholarship Fund during Fish-Off)

5:00pm: Round Two Contestants Check in at the registration table to pick up the name tag and event shirt.

6:30pm: Sloppy Joe’s 43rd Annual Hemingway Look-Alike Contest - Preliminary Round Two on stage at Sloppy Joe’s. Contestants will be narrowed down to approximately 12 finalists to advance to Saturday night’s final round. (Live Auction benefiting the HLAS Scholarship Fund immediately following preliminary round two while awaiting results)

Date: July 17-21, 2024