Hemingway Days
Hemingway Days to Honor Ernest in Key West July 23-27, 2025
KEY WEST, Florida Keys — Ernest Hemingway look-alikes, writers, anglers, and fans of the late author’s work are to gather in Key West Wednesday through Sunday, July 23-27, 2025, for the annual Hemingway Days celebration. The festival honors the legacy of the American literary giant who lived and wrote on the island for most of the 1930s.
Scores of stocky, bearded men resembling Ernest are to compete in the annual Hemingway® Look-Alike Contest at Sloppy Joe’s Bar, 201 Duval St., a frequent hangout for the legendary writer during his Key West years.
Other festival events include the wacky “Running of the Bulls,” a presentation on 1930s Key West, a commemoration of the 126th anniversary of Ernest’s July 21 birth, a museum exhibit of rare Hemingway memorabilia, a three-day marlin tournament recalling his passion for deep-sea angling, literary readings, a street fair celebrating the island’s lively spirit, and a 5k run and paddleboard race that salute Hemingway’s sporting interests. Associated with the festival is the Lorian Hemingway Short Story Competition coordinated by Ernest’s author granddaughter.
Ernest Hemingway wrote many of his best-known works in the second-story studio that adjoins his former Key West home — now a museum — at 907 Whitehead St. Among them were “Death in the Afternoon,” “For Whom the Bell Tolls,” “The Snows of Kilimanjaro” and “The Short Happy Life of Francis Macomber.” Hemingway even used Depression-era Key West as the setting for his widely acclaimed novel “To Have and Have Not.”
Both his literary prowess and his exuberant Key West lifestyle are commemorated during Hemingway Days.
Hemingway Days Updates & Information
- Hemingway Mystique Remains at Key West Sites
- Literary Landmarks Showcase Key West's Creative Heritage
Hemingway Days Founder Michael Whalton Recalls Festival’s Origin
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. Read More
Photos from the 2023 Hemingway® Look-Alike Contest and Events
Previous Hemingway Look-Alike Contest winners Zach Taylor (left) and Jon Auvil (right) congratulate Gerrit Marshall for winning the 2023 contest at Sloppy Joe’s Bar in Key West, Fla. After 11 years of competing. Marshall achieved success on his 68th birthday. The competition was a highlight of the annual Hemingway Days festival. (Andy Newman/Florida Keys News Bureau)
Gerrit Marshall (center) hoists his trophy after winning the 2023 Hemingway Look-Alike Contest at Sloppy Joe’s Bar in Key West, Fla., on his 68th birthday. Flanking Marshall (from left) are previous winners including Tom Grizzard, Wally Collins and John Stubbings. The competition was a highlight of the annual Hemingway Days festival saluting literary legend Ernest Hemingway, who lived and wrote in Key West during most of the 1930s. (Andy Newman/Florida Keys News Bureau)
Chris Dutton gazes at a photograph of Ernest Hemingway, taken while the author lived in Key West during the 1930s, as he competes in the 2023 Hemingway Look-Alike Contest at Sloppy Joe’s Bar in Key West, Fla. Dutton made the competition finals as a “young Hemingway,” but did not win. The contest was a highlight of the annual Hemingway Days festival. (Andy Newman/Florida Keys News Bureau)
A cat dubbed Leonardo da Vinci rests atop an antique typewriter at the Ernest Hemingway Home & Museum on Whitehead Street in Key West, Fla. Hemingway lived and wrote at the home for most of the 1930s, penning some of his best-known works. Now a registered National Historic Landmark, the home is a museum honoring the author — and a haven for several dozen cats, many of them with six toes and descended from a sea captain’s feline given to Hemingway. (Rob O'Neal/Florida Keys News Bureau)
For high-resolution photos of Hemingway Days for media use, visit media.fla-keys.com.