Hemingway Days Festival
The Hemingway Days Festival 2026 celebrates the 127th anniversary of Ernest Hemingway’s birth, honoring the Nobel Prize-winning author who called Key West home during the 1930s. This year marks the 45th annual celebration of his literary legacy, adventurous spirit, and larger-than-life persona.
Festival Dates: July 21 – July 26, 2026
While small commemorative events begin on Hemingway’s actual birthday (July 21), the core festival and the world-famous Look-Alike Contest run from Wednesday through Sunday.
Signature Events & 2026 Schedule
The festival is a blend of high-stakes sport, literary high-brow, and quirky island fun.
| Event | Date | Location | Description |
| Papas Meet & Greet | Wed, July 22 | Sloppy Joe’s Bar | The first chance to meet the “Papas” (contestants and past winners). |
| Look-Alike Contest (Rounds 1 & 2) | July 23–24 | Sloppy Joe’s Bar | Bearded hopefuls compete to prove they most resemble “Papa” Hemingway. |
| Key West Marlin Tournament | July 22–25 | Perry Hotel & Marina | A three-day big-game fishing tournament with over $50,000 in prizes. |
| Running of the Bulls | Sat, July 25 | Duval Street | A wacky, Key West version of the Spanish tradition featuring man-made bulls. |
| Look-Alike Finale | Sat, July 25 | Sloppy Joe’s Bar | The main event! One contestant is crowned “Papa 2026.” |
| Hemingway 5K Sunset Run | Sat, July 25 | Southernmost Point | A scenic run through Old Town followed by a post-race beach party. |
| Papa’s Birthday Bash | Sun, July 26 | Sloppy Joe’s Bar | A farewell celebration with cake and Bloody Marys with the Papas. |
Festival Highlights
The Look-Alike Contest: This is the festival’s crown jewel. Dozens of stocky, bearded men in safari shirts and wool sweaters (despite the July heat) descend on Sloppy Joe’s—Hemingway’s favorite watering hole—to channel the author.
Lorian Hemingway Short Story Competition: For those who prefer the pen to the rod, this prestigious competition (directed by Ernest’s granddaughter) recognizes emerging writers from around the globe.
Caribbean Street Fair: On Saturday, Duval Street transforms into an open-air market with local arts, crafts, food, and live music, coinciding with the “bull” run.
The Hemingway Home & Museum: While not a “festival event” per se, the museum remains the spiritual center of the week, where visitors can see the author’s writing studio and the famous six-toed cats.
Pro-Tips for 2026
Beat the Heat: July in Key West is famously humid. If you’re watching the outdoor “Running of the Bulls” or the 5K, stay hydrated and seek shade whenever possible.
Arrive Early: For the Look-Alike Contest at Sloppy Joe’s, the bar reaches capacity hours before the 6:30 PM start time. There is no reserved seating—it’s standing room only and high energy.
Dress the Part: While not as costume-heavy as Fantasy Fest, “Papa” attire (safari gear, fisherman sweaters, or 1930s island wear) is highly encouraged and adds to the immersion.
