Key West · July
Hemingway Days
Every July, Key West celebrates its most famous former resident with Hemingway Days: six days of literary events, fishing lore and the spectacle the week is known for, the Ernest Hemingway Look-Alike Contest at Sloppy Joe's, where more than a hundred white-bearded men compete to be crowned Papa.
The 2026 festival runs Tuesday, July 21 through Sunday, July 26, timed as always to Hemingway's July 21 birthday. The contest anchors the week, but the Saturday street fair on Duval, the comic Running of the Bulls and a 5K fill out a schedule that takes over Old Town.
Quick Facts
- Dates
- July 21 to 26, 2026
- Main event
- Look-Alike Contest finals, Saturday, July 25, 6:30 p.m., Sloppy Joe's
- Street fair
- Saturday, July 25, 10 a.m. to 10 p.m. on Duval
- Also
- Running of the Bulls, Hemingway 5K and paddleboard race
- Cost
- Most events free to watch
- Since
- 1981
The Look-Alike Contest
This is the one you have seen photos of: a stage at Sloppy Joe's packed with stocky, white-bearded men in fishing sweaters, each making his case to become the year's official Papa. Preliminary rounds run Thursday and Friday nights, July 23 and 24, with the finals Saturday, July 25 at 6:30 p.m. Many contestants come back year after year; winning on the tenth try is a badge of honor.
Fair warning: Sloppy Joe's holds only so many people and half the island wants in. Show up very early for the finals or settle for the crowd spilling onto Duval, which is its own kind of fun.
The rest of the week
Saturday, July 25 is the big day beyond the bar. A street fair runs 10 a.m. to 10 p.m. on Duval with vendors, food and music. At 1 p.m. the Running of the Bulls sets off, Key West's answer to Pamplona: look-alikes in sashes wheeling wooden bulls on wheels through the streets while the crowd hams up the danger.
- · The Hemingway 5K and a paddleboard race round out the weekend of July 25 and 26.
- · Literary events, readings and the Lorian Hemingway Short Story Competition run through the week.
- · The Hemingway Home on Whitehead Street is a must-visit any week, but book the tour early during the festival.
- · Late July is the hottest stretch of the Keys year. Hydrate like it is your job and plan indoor breaks.
Why Key West celebrates him
Hemingway lived and wrote here through the 1930s, and the town has never let go of him. The festival started in 1981, founded by Michael Walton with Sloppy Joe's, the bar Hemingway actually drank in. It has since funneled more than $275,000 into scholarships for Monroe County students through the look-alike society, which is the quiet good deed behind the beards.
Want more on Hemingway Days?
Official details from the organizers, plus Keys Weekly's coverage from the newspaper.
Frequently Asked Questions
When is Hemingway Days 2026?
Tuesday, July 21 through Sunday, July 26, 2026, in Key West, with the Look-Alike Contest finals Saturday, July 25 at 6:30 p.m. at Sloppy Joe's.
Is the Look-Alike Contest free to watch?
There is no admission charge at Sloppy Joe's, but space is first-come and the finals pack the bar hours ahead. Arrive very early or watch the overflow scene on Duval.
What is the Running of the Bulls?
A tongue-in-cheek homage to Pamplona: look-alikes push wooden bulls on wheels through the streets around Sloppy Joe's at 1 p.m. on Saturday. Nobody is in danger except the occasional beer.
How hot is Key West in late July?
Very. Expect low 90s with heavy humidity. The festival schedule leans on evenings for a reason. Drink water and take the afternoon slow.
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