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Channel Your Inner Hemingway at the Key West Look-Alike Contest

If you’re sporting a beard you might want to make your way South to the end of Route 1 for the Ernest Hemingway look-alike contest.

For 45 years contestants who are often heavy-set men largely wearing khaki shorts and fishermen’s sweaters, travel to Key West for the yearly event at Hemingway’s iconic watering hole “Sloppy Joe’s”, on the corner of Duval and Greene Street since 1937.

Hemingway moved to the island in 1928 where he lived until late 1939 writing, fishing and drinking.

For an only $35 entry fee you’ll be joining over a hundred bearded “Papa” hopefuls from around the globe competing to claim the title during the 6 day Hemingway Days Celebration.  

There’s a full schedule of events July 22-26 where you can walk in his footsteps amongst a mostly rowdy group of characters.

In a nod to Hemingway’s love for Spain and it’s traditions, there is a playful “Running of the Bulls” Key West style with wooden saw-horses on wheels. It’s a spectacle filled with humor and camaraderie encapsulating the free loving spirit of the event.

Since Hemingway had a passion and love for the sea, there is the Key West Marlin Tournament offers anglers a chance to compete for $50,000 in cash prizes.

There’s even an Arm Wrestling contest, a Caribbean street fair and assorted events at restaurants throughout the island. 

Of course there is Hemingway’s former residence, which is now a museum celebrating his 127th birthday.

The Hemingway Look-alike Society is much more than just a group of portly gray-haired old men. It inspired the creation of a scholarship program that has provided $350,000 in financial assistance to students attending the College of the Florida Keys.  

So come on down to celebrate the man’s life and enduring legacy of the one of the greatest literary figures of the twentieth century and see if your favorite “Papa” won.

David Garland Jul 14, 2026 Key West FL Bars Events Places to Visit

Location: Off, 201 Duval St, Key West, FL 33040, USA
David Garland
David Garland
Jul 14, 2026
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