Key West Hemingway Days is a week-long July festival built around the island's most famous former resident. From 1928 to 1940, Ernest Hemingway called this place home, wrote some of his best work here, and left behind a reputation that still walks a few steps ahead of him. The week mixes literary events, a serious sportfishing tournament, the tongue-in-cheek running of the bulls, and the marquee event — the Hemingway Look-Alike Contest at Sloppy Joe's, his old haunt.
What Hemingway Days Is
Think of it as history, sport, and literature rolled into one week. The island celebrates its most famous resident with events that nod straight to his own obsessions: deep-sea fishing, bullfighting, writing, and cats — he was handed a six-toed cat by a ship's captain, and that cat's descendants still prowl the Hemingway Home. Expect it in the back half of July, roughly the last full week, in 2026.
Key Events: The Running of the Bulls
For most first-timers the running of the bulls is the hook — a satirical, Key West-flavored take on the Pamplona tradition. Picture costumed "bulls" and runners on a short course through Old Town, nothing like the real thing in Spain. It's lively, it's silly, and it pulls a crowd. Runners are a mix of locals and visitors who sign up ahead. Get there early for a spot along the route, especially if you want photos.
Key Events: The Look-Alike Contest
The headliner is the Hemingway Look-Alike Contest at Sloppy Joe's — Papa's old bar. Rooms full of stout, white-bearded men in chunky fisherman sweaters (in July, no less) compete across several nights to be crowned the best Hemingway double. It's one of the great oddball spectacles on the Keys calendar and a genuine blast to watch. The finals usually land toward the end of the week. Trust me on this one.
Key Events: The Fishing Tournament
The Key West Hemingway sportfishing tournament runs right alongside the festival — a real deep-water event that draws experienced anglers. Hemingway was an obsessive offshore fisherman who credited it with keeping him steady, and the tournament carries that legacy forward. If you're into fishing, it's reason enough to time your trip for late July.
Key Events: The Short Story Contest
The Hemingway short story competition pulls writers from all over the country. Finalists get announced during festival week and winners read at the San Carlos Institute. It's quieter than the sports side, but for writers it's the main draw. You don't have to be in town to enter — the contest opens in spring.
The Hemingway Home and Museum
The Hemingway Home and Museum is open daily year-round and worth a stop festival or not. The house sits largely as he left it, the gardens are lush, and the cats — roughly 40 to 50 polydactyl cats named after famous figures — roam wherever they please. The six-toed line descends from Snow White, the first cat Hemingway was given. Tours run continuously and admission helps maintain the property. Bonus: it's air-conditioned, which matters a lot in July.
Tips for Attending
Hemingway Days draws a crowd, but it stays manageable — you're unlikely to hit the total sell-out that Fantasy Fest creates. That said, late July is hot and sticky. Wear sunscreen, drink water, and load your outdoor events into the morning. The running of the bulls happens early in the week, so check the schedule and be there for it.
How It Compares to Other Key West Festivals
Fantasy Fest is bigger, wilder, and more intense. Lobsterfest is food-first and casual. Hemingway Days draws literary types, fishing folks, and cat people — the most niche of the three. Here's the move: come for the history AND catch the human theater at Sloppy Joe's. Chasing a full-tilt party instead? Fantasy Fest is your week.
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When is Key West Hemingway Days 2026?
Hemingway Days runs in mid-to-late July — figure the back half of the month, roughly the last full week, in 2026. The marquee events, the running of the bulls and the Hemingway Look-Alike Contest at Sloppy Joe's, usually fall midweek and toward the weekend. Check the official Key West Hemingway Days site for the confirmed 2026 schedule.
What's the running of the bulls in Key West?
It's a satirical, scaled-way-down take on the Pamplona running of the bulls, nodding to Hemingway's years in Spain. In Key West, small groups get led through the streets by costumed bull-handlers while runners jog alongside. It's fun, not dangerous — the 'bulls' are people in costume and the route is short. Think block party with a little running, nothing like the Spanish original.
How many Hemingway cats are at the Hemingway Home?
The Hemingway Home and Museum keeps roughly 40 to 50 polydactyl (six-toed) cats, each named after a famous figure. As cats pass, new ones carry the tradition on. They roam the grounds freely and are the main draw for a lot of visitors. The house and cats are open for tours daily, and admission supports preservation of the property.
Is Hemingway Days family-friendly?
Yes, more than Fantasy Fest. The Key West running of the bulls is family-friendly. The literary events (short story contest, readings) are small and fine for all ages. The Hemingway Look-Alike Contest at Sloppy Joe's is a fun spectacle, though it's a bar event, so gauge it by your kids' ages. The fishing tournament is out on the water, and the crowds are present but much smaller. A solid fit for families into history or literature.