Key West Festivals & Events

Sloppy Joe’s 44th Annual Hemingway Look-Alike Contest

Name: Sloppy Joe’s 44th Annual Hemingway Look-Alike Contest
Start: 2025-07-23T18:00:00-04:00
End: 2025-07-27T18:00:00-04:00
Location: Sloppy Joe’s Bar

When: July 23 - July 27, 2025

Where: Sloppy Joe’s Bar, 201 Duval St, Key West, FL 33040

Discover the Hemingway Look-Alike Contest in Key West

Sloppy Joe's hosts the 44th Annual Hemingway Look-Alike Contest from July 23-27, 2025 in Key West. This celebrated event showcases a week of engaging activities that honor Hemingway's enduring legacy. On Wednesday, July 23, 2025 at 5:00pm, guests can attend a Meet & Greet with the Papas at Sloppy Joe's. The festivities continue on Thursday, July 24, 2025 with the 6:30pm Look-Alike Contest – Round One, followed by another round at 6:30pm on Friday, July 25, 2025.

The excitement reaches its peak on Saturday, July 26, 2025 with a series of events: a Noon Photos with Papas session, the exhilarating 1:00pm Running of the Bulls, and the 6:30pm Look-Alike Contest FINAL ROUND to crown Papa 2025. The week concludes on Sunday, July 27, 2025 with a Papa Birthday Bash, with the exact time to be determined.

Additional details about the Hemingway Look-Alike Society auction and complimentary events are available at keywestlookalikes.com. This event promises a unique blend of literary tribute and vibrant local culture, making it a must-attend celebration in Key West.

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