Each July on the birthday of Key West’s most famed writer, hundreds of white-bearded, cocktail-slinging Ernest Hemingway doppelgangers take to the streets for a mock bull run and then to the stage with song and dance at Sloppy Joe’s Bar. For visitors, there’s great history and enjoyable events everywhere you look.

For an inside look at the July 21–26 annual tribute’s many events and enjoyable vibe – and tips on how to win – we picked the brain of the 2013 winner, Stephen Terry.

All photos © Chuck Wagner

Were you always destined to be an Ernest Hemingway look-alike, or did you wake up one day with the realization and a white beard?

I actually had a beard most of my adult life, but it was red. When my daughter was born, I shaved it off. When it grew back, it was white. I’d been going down to Key West for a number of years and remembered seeing the contest go on one year. So finally, one year I hounded my wife enough to go and I entered.

Was Hemingway Days what you expected?

I first went in 2007. I didn’t know what I was doing. You’re competing against 150 different guys, but you’re not just competing; you become friends with them, start looking forward to seeing them every year. You’re sad you didn’t win, but happy your friend did.

They’re looking for you to be a good guide, to further the scholarship society, but they’re also picking their drinking buddies for the next 20 years.

“At the end of the day, it’s a beauty contest for old guys.” – Stephen Terry, 2013 Hemingway Look-Alike Contest Winner

So there’s a strategy to being picked?

Sure. One thing is finding a guy who looks like Hemingway. There are a lot of men with white beards, but it’s a smaller percentage who actually look like the man. Personality wise, they want someone who is responsible, relatively level-headed, and who can represent the Look-Alike Society well. Keep in mind, our biggest goal is raising money for the scholarship funds.

If you make it to the finals, you end up giving three different speeches of varying lengths on why you should be chosen. The funny thing is, you prepare all those speeches, but you don’t prepare for the speech if you win. I struggled through mine, barely remember it. Luckily the reporters ask leading questions.

Is holding your alcohol key criteria?

Hemingway was a big drinker, and many think if you act the same way, you’ll get in, but that’s not everything. They tend to stay away from the guys who go up and do the contest drunk.

Any secrets to getting noticed, to set yourself apart from the ocean of white beards?

Everyone’s looking for an edge; most bring a prop. Live animals are forbidden. You can’t bring a cat or a parrot up, but people bring other props. One contestant has a fake finger he wears, walking around with six fingers on one hand [a nod to Hemingway’s polydactyl cats]. He never says anything about it, but you notice it.

So, be moderate on the drinking, prepare a speech, and leave the cats at home. But what do you wear to become Hemingway?

After the beard? A khaki colored fishing shirt and khaki shorts. There are a few die-hards who wear a wool fishing sweater, but it’s definitely very hot wearing it in Key West in July. I think I lose five pounds every time I do it. The key is finding a nice AC vent and let it flow over your head, then you can get through anything.

Hemingway Days Picks

Hemingway in Key West

Learn about the famous author’s fascinating life, his epic battles with fish (and sharks), and check out photographs and memorabilia you won’t find anywhere else.

Meet the Authors

You won’t meet Hemingway, of course, but there are a dozen well-known writers who will offer readings, book signings, and tales of how the bearded legend inspired their own literary careers.

Running of the Bulls

You aren’t particularly likely to be gored in this bull run, but you will get to join previous “Papas” and current event-goers on a lighthearted romp through downtown Key West.

Key West Marlin Tournament

There were few things Hemingway enjoyed as much as fishing, and this huge tournament offers up to $50,000 in cash prizes for attempting to reel in some of the monsters of the deep that the author once wrestled with.

Lazy Dog Paddleboard Race

Take a break from all things Hemingway, and enjoy a vigorous three-mile paddle along the Key West coastline, with the key’s sunny southernmost beach awaiting finishers.

Where to Stay Margaritaville Key West Resort & Marina | Sunset Key Cottages