Sloppy Joe's Bar Proudly Presents

44th Annual Hemingway® Look-Alike Contest

July 23rd - 27th, 2025 in Key West, Florida

Key West’s Most Whimsical Tribute to Papa Hemingway

Welcome to the official webpage of the Hemingway Look-Alike Contest, Key West’s most iconic and whimsical tribute to one of the greatest literary figures of the 20th century, Ernest Hemingway. Held annually in sunny Key West, this event celebrates Hemingway’s life in Key West and enduring legacy in a way that’s as unique and spirited as the man himself.

At the heart of the festivities is the Hemingway Look-Alike Contest, where participants worldwide don their best Hemingway-esque attire and compete to be named “Papa.” This isn’t just a contest of physical resemblance; it’s a celebration of Hemingway’s larger-than-life persona. Contestants are judged not only on their physical similarity to the great writer but also on their embodiment of his spirit and zest for life.

Adding to the excitement is the playful “Running of the Bulls” event, a nod to Hemingway’s love for Spain and its traditions. But in true Key West style, we swap real bulls for wooden sawhorses on wheels. It’s a spectacle filled with humor and camaraderie, perfectly encapsulating the fun-loving spirit of both Hemingway and Key West.

This event isn’t just for Hemingway enthusiasts or look-alikes; it’s a gathering that invites all to enjoy the vibrancy of Key West, the thrill of friendly competition, and the warmth of a community that knows how to celebrate life. Whether you’re a literature buff, a Hemingway admirer, or just searching for a good time, the Hemingway Look-Alike Contest is an experience you won’t want to miss.

Features of the Event:

  • Look-Alike Contest: A spirited competition where the resemblance to Hemingway is just the beginning.
  • Running of the Bulls: A humorous twist on a Spanish tradition, with Key West’s unique charm.
  • Celebration of Hemingway’s Legacy: Immerse yourself in the world of Ernest Hemingway through stories, and an atmosphere that echoes his adventurous life.
  • Community and Camaraderie: Meet fellow Hemingway fans and become part of a tradition that celebrates one of literature’s giants in the most joyous way possible.

 

Join us for an unforgettable event where the spirit of Ernest Hemingway is alive and well, and the essence of Key West’s fun-loving culture is on full display. We can’t wait to see you here!

Event Highlights

The Hemingway Look-Alike Contest comprises many activities. Below are some examples. See the full schedule for details.

Look-Alike Contest

The event that started it all! Come to Sloppy Joe's to join the festivities and cheer on your favorite 'Papa'.

Sloppy Joe's Bar, Key West, Running of the Bulls at Hemingway Look-Alike Contest

The Running of the Bulls

On Saturday, come watch the laugh-filled Running of the Bulls. A wacky, Key West take from the famous event in Pamplona, Spain.

Hemingway Caribbean Street Fair

Street Fair

On Saturday, Duval Street is filled with vendors of all types: arts, crafts, food, and drinks. All benefiting the Literacy Volunteers of America, Monroe County.

Marlin Tournament

Celebrating its 42nd year, the 2024 Key West Marlin Tournament, featuring $50,000 in cash prizes in the Marlin Division and more in the Fun Fish Division, is set for July 17 – 20, 2024.

Some of Our Amazing Sponsors