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Everything you need to know about the Conch Republic. Keep up on local events, nightlife and activities while in Key West.

The Gates Guide to Hemingway Days in Key West

The Gates Guide to Hemingway Days in Key West

June 26th, 2019 | Key West Events & Festivals

Ernest Hemingway wasn’t just an American icon, he was a Key West icon. The famed literary giant spent much of his time on the island, living in the Spanish colonial on Whitehead. There he penned some of his most successful novels, like A Farewell to Arms and Death in the Afternoon.

Every July it’s Key West tradition to celebrate Hemingway, commemorating his birthday with the week-long festival Hemingway Days. Hemingway Days is a culmination of all things Papa, with cultural events, fishing tournaments, look-alike contests, and more. If you’re visiting Key West from July 16-21, it’s an especially fun way to brush up on your Hemingway knowledge and see the island at the same time.

Here are the events you can’t miss at Hemingway Days 2019:

The Key West Marlin Tournament, July 17-20

Considering that Papa Hemingway was an avid angler, it only makes sense that the annual Key West Marlin Tournament is held during Hemingway Days. The tournament is three days of fishing, with evening weigh-ins at the Stock Island Marina Village. First-prize winners take home $25,000 in cash.

Key West Art & Historical Society’s Hemingway mini-Symposium, July 16

Hemingway history buffs and culture junkies: this is an event you don’t want to miss. The KWAHS Hemingway Symposium provides expert insight from Hemingway biographers and archivists such as Robert K. Elder, author of Hidden Hemingway: Inside the Ernest Hemingway Archives of Oak Park, and Brewster Chamberlin, of Facts and Fiction in the Hemingway Industry. Admission is $5 for non-members, free for KWAHS members.

Hemingway Look-ALike Contest @ Sloppy Joe’s, July 18-20

One of the most eye-catching events of Hemingway Days, the Hemingway Look-Alike Contest is hosted by none-other than Sloppy Joe’s, Papa’s go-to bar during his days in Key West. Hundreds (yes, hundreds) of Papa look-alikes come from all over the world to compete.  Frankly, it’s quite surprising to see just how many Hemingway doppelgangers exist. Come see for yourself. The final round will be judged on Saturday, July 20 at 6:30 p.m.

Running of the Bulls on Duval, July 20

This is one of our favorites. Every year the Papa look-alikes from years past return to Key West for the “Running of the Bulls” on Duval Street. Fortunately, this isn’t an ordinary running of the bulls, but a leisurely stroll with the bulls (in true Key West fashion). Think hundreds of Hemingways, all dressed in their Pamplona red and white, steering plastic bulls on wheels down Duval. It’s definitely a sight to see. Grab a daiquiri and join in on the fun. 

Sloppy Joe’s Arm-Wrestling Contest, July 21

Papa Hemingway enjoyed refereeing boxing matches in what is now Blue Heaven back in the day. The next best thing during Hemingway Days is a good, old-fashioned arm wrestling tournament at Sloppy Joe’s Bar..Sip on a bloody mary and watch the tournament for free, or join in with a $5 entry. Prizes divvied up according to winners of each weight category! Registration at 10 am; contest at 11 am. See details.

Start Planning Your Trip to Key West

If you’re thinking about a visit to Key West, don’t delay! It’s always summer in the Conch Republic. The Gates Hotel is a Condé Nast award-winning hotel located in New Town, which offers free hourly shuttle service to Old Town. Exciting onsite amenities – like a food truck, cigar lounge, and a spectacular swimming pool – puts The Gates in its own special category. Check out our special offers online.

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