Hemingway Days to Celebrate Literary Legend July 18-23 in Key West

Keys History
This Keys History story spotlights an historically focused attraction, event, person or place that enriches the Florida Keys

KEY WEST, Florida Keys — Ernest Hemingway fans can celebrate the late author’s literary accomplishments and colorful Key West lifestyle Tuesday through Sunday, July 18-23. The annual Hemingway Days festivities salute the legacy of the Nobel Prize winner who lived and wrote on the island for most of the 1930s.  

Events include the famed Hemingway® Look-Alike Contest, presentations covering aspects of the author’s Key West years, the tongue-in-cheek “Running of the Bulls,” a reading of his little-known poetry and a commemoration of his July 21 birthday, running and paddleboarding challenges that salute Hemingway’s sporting lifestyle, an exuberant street fair and a high-stakes three-day marlin tournament that recalls his passion for Florida Keys angling. 

The festival officially begins Tuesday, July 18, with a lecture by Rebecca Johnston, president of the Florida Hemingway Society, focusing on Hemingway’s connection to a 1935 hurricane that influenced his Key West novel “To Have and Have Not.” Among other highlights are a happy-hour presentation on Hemingway’s life in the island city by Cori Convertito, curator and historian for the Key West Art & Historical Society. For additional information, visit  kwahs.org/education/adult-programs/hemingwaydays. 

Hemingway Days’ most colorful event is Sloppy Joe’s annual Hemingway® Look-Alike Contest. Past winners choose the new “Papa” from 125 or more stocky, bearded contestants at Sloppy Joe’s Bar, 201 Duval St., a watering hole frequented by the author. Preliminary rounds are scheduled at 6:30 p.m. Thursday and Friday, July 20 and 21, with the final round Saturday, July 22. Visit sloppyjoes.com/hemingway-look-alike-contest/. 

The “Papas” also enliven other festival events including Saturday’s infamous “Running of the Bulls.” Set for 1 p.m. outside Sloppy Joe’s with manmade bull replicas, the offbeat event recalls Hemingway’s fascination with the bull ring. 

Anglers can emulate “Papa’s” devotion to deep-sea fishing during the Key West Marlin Tournament, set for Wednesday through Saturday, July 19-22. Participants can pursue marlin and spearfish, sailfish, tuna, dolphin fish and wahoo while competing for $50,000 in guaranteed cash prizes. For information and registration, visit keywestmarlin.com.  

Held in conjunction with the festival is the Lorian Hemingway Short Story Competition coordinated by  Ernest Hemingway’s author granddaughter. Each year the contest winners are announced — and the top story given its first public reading — during Hemingway Days. Visit shortstorycompetition.com for contest details.

Other Hemingway Days events include the 5k Sunset Run and Paddleboard Race and a lively Saturday street fair on Key West’s Duval Street, where the island’s most famous literary resident once walked. 

Festival information: hemingwaydays.net 

Jon Auvil, center, receives an Ernest Hemingway bust and congratulations after he won the 2022 Hemingway Look-Alike Contest at Sloppy Joe’s Bar in Key West. Photo: Andy Newman

Jon Auvil, center, receives an Ernest Hemingway bust and congratulations after he won the 2022 Hemingway Look-Alike Contest at Sloppy Joe’s Bar in Key West. Photo: Andy Newman

The festival includes Key West's version of Pamplona, Spain's Running of the Bulls, with fake bulls-on-wheels pushed down Duval St. by Hemingway Look-Alike contestants. Photo: Andy Newman

The festival includes Key West's version of Pamplona, Spain's Running of the Bulls, with fake bulls-on-wheels pushed down Duval St. by Hemingway Look-Alike contestants. Photo: Andy Newman

Anglers in the Key West Marlin Tournament can emulate Papa Hemingway's devotion to deep-sea fishing.

Anglers in the Key West Marlin Tournament can emulate Papa Hemingway's devotion to deep-sea fishing.

This article was updated on July 17, 2023 at 5:20 PM
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