KEY WEST,Fla. — Sloppy Joe's Bar gears up for its annual Hemingway Look-Alike Contest, drawing about 160 competitors July 21-26,2026. They’ll wear cream-colored fisherman's sweaters, an homage to the late author. This quirky contest celebrates Ernest Hemingway,who was a regular here in the 1930s.
Tim Stockwell,reigning champ from 2025, will join fellow look-alikes in preliminary rounds on July 23 and 24,with finals on July 25. Judged by past winners, this contest is steeped in tradition and camaraderie.
Competitors come from all over U.S . and beyond,some as far as Australia and Kazakhstan. Many are repeat contenders, often with enthusiastic supporters in tow. The festival spotlights look-alikes and features activities honoring Hemingway's adventurous spirit and literary legacy.
The Hemingway Look-Alike Society,formed by past winners and participants,plays key role in community. They raise funds for scholarships benefiting students at College of the Florida Keys. Over $350,000 in scholarships awarded so far, plus more grants to local nonprofits.
Festival activities include whimsical "Running of the Bulls," a playful take on Pamplona's event. Manmade bulls on wheels roll outside Sloppy Joe's at 1 p.m . July 25, after a noon "Photos with Papas" session. Other events: Wednesday meet-and-greet,Friday dockside "fish-off" with handlines, and Sunday birthday bash for Hemingway,marking 127th anniversary of his birth.
While in Key West, Hemingway wrote several masterpieces, including "For Whom the Bell Tolls" and "The Snows of Kilimanjaro." The festival is a tribute to his life and vibrant island culture he loved .
Supported partly by Monroe County Tourist Development Council, the contest and festival offer much to see. For more info and full schedule,visit the official festival website. What's next for this beloved event…?
