Do You Look Like Ernest Hemingway? There’s a Festival for That

Celebrate Hemingway’s 125th birthday alongside hundreds of dudes who look like him.

Hemingway Days Festival Key West Florida
Dusty Rhodes (center) has competed in the look-a-like contest 12 times. | Photo by Andy Newman/Florida Keys News Bureau
Dusty Rhodes (center) has competed in the look-a-like contest 12 times. | Photo by Andy Newman/Florida Keys News Bureau

Summer sweat glistens on the contestants’ brows and anticipation builds as the announcer drops the starting flag. The running of the bulls begins, as a sea of men sporting red berets, white shirts, and silver beards charge shoulder to shoulder down Greene Street in downtown Key West.

The scene is reminiscent of Spain, except the contestants are not actually running from anything. The only bovines here are made from old rum barrels with wooden bull heads mounted on wheels. Some contestants ride atop, while others somewhat laboriously help push and pull them along. It’s not an actual bull run, but a parade for Hemingway Days, a celebration of one of Key West’s most famous residents, author Ernest Hemingway, aka Papa.

“Most of these guys are no longer young, so it’s not like they actually run,” says Carol Shaughnessy, a longtime Key West resident who’s been working with the festival since its founding. “It’s more like an amble with the bulls. But they do wear the Pamplona outfits and thousands of people gather on the street to watch and cheer.”

The running of the bulls is just one highlight in the six-day festival in Key West, which takes place every year around the author’s birthday. This year’s festival runs from July 16–21, celebrating what would have been Papa’s 125th, including a special birthday bash on the last day.

The event is perfectly in step with the town’s eccentric reputation. Each year, 150 or so grown men dress up in Hemingway-inspired garb—think safari khakis and wool fisherman sweaters—and overtake the streets of Key West, holding down bar stools and competing in the largest Hemingway lookalike contest in the world.

“It’s been called a beauty contest for paunchy older guys, but that really doesn’t do it justice,” says Shaughnessy.

Hemingway Days Festival bull running
Photo courtesy of Hemingway Days

It began in 1981 as a way to lure summer tourists to Sloppy Joe’s bar, which was the author’s favorite haunt when he lived in Key West during the 1930s. Since then, the event has grown to become a major spectator sport, where thousands of people come to cheer on jovial bearded men vying for attention. The week also includes a Caribbean street fair, paddle board race, 5K run, and marlin fishing tournament. For those who’ve come to actually celebrate his prose, there are literary readings, an associated short story competition, and a special museum exhibit featuring rare memorabilia, including his blood-stained WWI ambulance driver’s uniform.

“It is such a good-spirited event, and a distillation of the best parts of Key West living,” says Shaughnessy. “It makes people smile and it celebrates both Hemingway's literary mastery and the Key West lifestyle that he loved. He lived large, and life was an adventure to him.”

During his time in Key West, and still today, Hemingway has been a controversial character. He instigated bar brawls, refereed and competed in boxing matches, stole the urinal at Sloppy Joe’s, hunted Nazi U-boats with hand grenades (didn’t find any, luckily for him), and otherwise widely aired his quick-witted humor and super ego. He went on to win both Nobel and Pulitzer Prizes, inspired generations of writers and adventurers, and helped Key West become a haven for other literary icons. His house-turned-museum and its many six-toed cats remain one of the town’s most popular tourist attractions.

The week’s apex is the lookalike contest at Sloppy Joe’s on Thursday, Friday, and Saturday nights. There, the Wannabes (contestants) throw out all of their tricks trying to impress the Papas (the judges, all previous winners) and flaunt their popularity with the audience.

“They don’t discourage bribery,” says Kathy Rhodes, the spouse of a famous Wannabe named Dusty Rhodes. “So the Wannabes give out T-shirts to spectators with their name on them, and free drink cards to get people to hold a sign and cheer for them.”

This year will be Dusty’s 12th try for the crown. With the signs and cheering sections, “it’s very much like a political convention,” he said. “But the reason we do it is for the camaraderie.”

Some have competed for decades. For others, it’s a once-in-a-lifetime shot. One year a contestant from Kazakhstan explained, through an interpreter, that it was his lifelong dream to enter and his entire village raised money to send him. He didn’t win, but at the end he held up a T-shirt signed by all of the guys and said it would become a treasure of his country and be placed in a museum.

Hemingway Days look-a-like competition
Photo by Rob Oneal

“I swear you can’t make this stuff up,” says Shaughnessy. “Seeing him on stage and realizing that something we think is fun, but normal for Key West, had such deep meaning for him, that just took my heart. There is so much more meaning to this festival than, ‘oh, I look like Hemingway.’”

The festival is a bit debaucherous, it's true, but it also attracts literary lovers and locals who want to do something good for their hometown. All proceeds from the festival, around $125,000 each year, support local scholarships for students pursuing literary- and nursing-related degrees, plus other Key West charities. Whether you’re a bookish Hemingway aficionado or prefer moonlighting as an illiterate rum-guzzler, Hemingway Days, like Key West, welcomes you.

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Karuna Eberl is a freelance writer and indie film producer, hailing form the sandbars of the Florida Keys to the high country of Colorado and beyond. Her beats match her life’s passions: outdoor adventure, travel, nature, conservation, and history. Recent outlets include Atlas Obscura, BBC Travel, Gear Junkie, National Parks Advocate, National Geographic Channel, and the Florida Keys Wildlife Society. She’s won numerous awards for her writing and films, including the documentary The Guerrero Project, about the search for a sunken slave ship off of Key Largo. She and her partner wrote Quixotic’s Key West & The Florida Keys Travel Guide and she is also author of the kids’ book All About the Everglades.