Aspiring 'Papas' to Vie for Hemingway Look-Alike Honors in Key West

KEY WEST, Fla., June 25, 2026 /PRNewswire/ -- For some 160 stocky, bearded men who gather in Key West in mid-July, donning a sweater won't be just a fashion statement or reaction to an ocean breeze. Wearing a cream-colored fisherman's sweater could mean the difference between victory and defeat in Sloppy Joe's 45th annual Hemingway^® Look-Alike Contest.

The highlight of Key West's annual Hemingway celebration, the contest takes place at Sloppy Joe's Bar, 201 Duval St., Ernest Hemingway's frequent hangout when he lived and wrote on the island during the 1930s.

Spectators can cheer for their favorite competitors during nightly rounds Thursday through Saturday, July 23-25, at Sloppy Joe's.

As well as the contest, the Hemingway festival features six days of activities recalling Key West's most famous literary resident. Set for July 21-26, it salutes the writing talent, sporting pursuits and colorful lifestyle of the American author who won both Pulitzer and Nobel prizes.

Past look-alike entrants have come from around the U.S. and as far away as Australia and Kazakhstan to compete in the quirky contest — dressing in safari garb, wool fisherman's turtlenecks and other attire associated with the "Papa" persona adopted by Hemingway in his later years. Many are repeat contenders, and most bring groups of supporters who lobby loudly for their victory.

Preliminary rounds are set for 6:30 p.m. Thursday and Friday, July 23 and 24, with the finals at 6:30 p.m. Saturday. The contest is judged by former winners including 2025's Tim Stockwell of Key West — who, like the author he resembles, pursues an adventure-filled life.

The contest is much more than a lighthearted gathering. The Hemingway Look-Alike Society, formed by winners and competitors, works year-round to raise money for scholarships for students attending the College of the Florida Keys. To date, the society has awarded more than $350,000 in scholarships. Additional grants are given to Keys nonprofits.

The look-alikes also take center stage during other festival activities — including Sloppy Joe's "Running of the Bulls," a spoof of the renowned annual run in Pamplona, Spain. More like a stroll than a sprint, the offbeat event features manmade bulls on wheels and begins at 1 p.m. Saturday outside Sloppy Joe's. It is preceded by the noontime "Photos with Papas" opportunity.

Events also include a Wednesday evening meet-and-greet where look-alikes mingle with fans, and Friday's fun-filled dockside "fish-off" using traditional handlines. On Sunday, Hemingway fans can join the look-alikes at Sloppy Joe's for a belated "birthday bash" commemorating the 127th anniversary of Hemingway's July 21 birth.

During his 1930s residence in Key West, the renowned author wrote "For Whom the Bell Tolls," "The Snows of Kilimanjaro" and "To Have and Have Not" among other literary classics.

The Hemingway Look-Alike Contest and festival is presented in part by the Monroe County Tourist Development Council. For further details and a full event schedule, visit www.keywestlookalikes.com.

Media Contact: Carol Shaughnessy
Phone: 305-797-0579
E-mail: [email protected]

SOURCE Sloppy Joe's Bar