Sheet 04 · Events & Festivals
Hemingway Days Key West 2027: Look-Alike Contest & Festival Guide
Hemingway Days Key West 2027 runs July 20-25. Complete guide: Look-Alike Contest at Sloppy Joe's, Running of the Bulls parody, Marlin Tournament, and hotel strategy.
Hemingway Days Key West is the annual July festival celebrating the writer’s birthday (July 21, 1899) and his Key West literary legacy. The festival has run since 1981 and centers on Sloppy Joe’s Bar, where the Papa Hemingway Look-Alike Contest drew 134 registered contestants in 2026, the year a Young Hemingway took the title for the first time. Many of the bearded Papas return year after year, and the regulars have their own fellowship, the Hemingway Look-Alike Society. Beyond the look-alikes, the week includes a Caribbean street fair, a Key West parody Running of the Bulls (with fake bulls on wheels), the Lorian Hemingway Short Story Competition reading, the Key West Marlin Tournament, and a Sunset Salute closing ceremony at Mallory Square. This guide is the complete Hemingway Days playbook with the 2027 dates, signature events, ticket pricing, where to stay during the week, and what to expect as a non-participant observer. Written by Key West locals who watch the bearded Papas arrive every July. It is the summer counterweight to Fantasy Fest, the island’s far rowdier October blowout.
You will get the 46th Annual Hemingway Days dates (July 20-25, 2027), how the multi-round Look-Alike Contest works, the Running of the Bulls, the Lorian Hemingway Short Story Competition winners’ reading, the Key West Marlin Tournament, free events vs ticketed events, hotel strategy, parking strategy for Sloppy Joe’s nights, and the answer to “can anyone enter the Look-Alike Contest?” (yes — but veterans dominate).
Key Takeaways
- 2027 dates: July 20-25 (46th Annual). Coincides with Hemingway’s birthday July 21, 1899.
- Headline event: Papa Hemingway Look-Alike Contest at Sloppy Joe’s Bar (201 Duval). In 2026 the preliminary rounds ran Thursday and Friday, July 23-24, and the final Saturday, July 25, each at 6:30 PM.
- Other signature events: Caribbean Street Fair, Running of the Bulls (parody), Lorian Hemingway Short Story Competition, Key West Marlin Tournament, Sunset Salute.
- Most events FREE to watch at Sloppy Joe’s and on Duval Street. Ticketed: Cooking School dinner, Hemingway 5K registration, Marlin Tournament entry.
- Book hotels early for festival week, and compare quotes for your exact dates.
- Many “Papas” return year after year, and past winners judge.
2027 Hemingway Days Dates & Schedule
46th Annual Hemingway Days runs July 20-25, 2027. The day-by-day program goes up on the Hemingway Look-Alike Society’s contest page and the festival schedule.
The festival traditionally falls during the week containing Hemingway’s birthday (July 21, 1899). Most events concentrate Thursday through Saturday; in 2026 the Look-Alike Contest final and the closing celebrations both fell on Saturday. For a quieter musical weekend earlier in the year, see the Key West Songwriters Festival.
Look-Alike Contest rounds — Sloppy Joe’s hosts two preliminary nights and a final. In 2026 they fell on Thursday July 23, Friday July 24 and Saturday July 25, all starting at 6:30 PM.
Saturday July 24, 2027 — Hemingway 5K Sunset Run.
July 21-24, 2027 — Key West Marlin Tournament. The awards banquet date is on the tournament’s schedule at keywestmarlin.com.
Papa Hemingway Look-Alike Contest
The headline event of Hemingway Days. Held at Sloppy Joe’s Bar, 201 Duval Street.
Format: Multi-round contest: two preliminary nights, then the final. All three 2026 rounds started at 6:30 PM, with the final on Saturday July 25.
Contestants: Bearded men in safari/fishing/casual clothing, most of them channeling Hemingway’s later years, though a Young Hemingway won for the first time in 2026. That year’s contest had 134 registered contestants. The Hemingway Look-Alike Society is the Papas’ own fellowship and raises scholarship money. Many “Papas” return year after year, gaining recognition and eventually becoming judges.
Judging: Past winners (“Papa” winners from previous years) serve as judges. The current year’s winner cannot re-compete the following year (becomes a judge in retirement from competition).
Rules: Contestants turn up in Hemingway garb and are judged on resemblance, stage presence and character; hats come off for judging. The current entry form lists who is eligible.
Free to watch. Sloppy Joe’s becomes packed during preliminary nights and especially the final night — arrive early to secure a viewing spot. Standing room overflow extends onto Duval Street.
Past notable winners: David “Bat” Masterson (2024), Gerrit Marshall (2023), Jon Auvil (2022), and many others over the 45 years of the contest.
The Mamas: Wives of “Papas” return each year as a social subgroup (“Mamas”) with their own meetups and gatherings during the week.
Charity component: The Hemingway Look-Alike Society funds scholarship programs and other charitable causes year-round.
Running of the Bulls (Key West Parody)
A Key West parody of the famous Pamplona event. Hemingway look-alikes parade through downtown Key West pushing life-size fake bulls on wheels — significantly safer (and sillier) than the original. Typically held mid-week of the festival.
Route: Down Duval Street and through Old Town. Free to watch from sidewalks.
Spectacle: One of the most-photographed moments of the entire festival. Bring a camera.
Lorian Hemingway Short Story Competition Reading
The Lorian Hemingway Short Story Competition (named for Ernest’s granddaughter) dates back to 1981. It accepts emerging-writer submissions year-round and announces winners during Hemingway Days.
Format: Winners read their short stories at the announcement. In 2026 that took place on July 21 at Williams Hall, 729 Fleming Street; the 2027 venue appears on the festival schedule.
Cost: The reading is separate from the daily Hemingway Home tours, so a museum ticket isn’t part of it. Look for admission details alongside the reading on the organizers’ schedule.
Best for: Literary fans, writers, anyone interested in emerging literary voices.
Key West Marlin Tournament
The festival’s offshore-fishing component. The 2026 tournament ran July 22-25 out of the Perry Hotel and Marina, and the 2027 edition is set for July 21-24; check the tournament’s site for the venue.
Prizes: $50,000+ in total prizes across multiple species categories.
Targets: Blue marlin (peak season July), white marlin, sailfish (catch-and-release).
Entry: Tournament boats register through the tournament organizers. Entry fees vary; spectators can watch weigh-ins for free.
Hemingway 5K Sunset Run & Paddleboard Race
Combines fitness with island views. Saturday late afternoon. Benefits Literacy Volunteers of America.
Cost: Adult registration for the July 24, 2027 race runs $46 to $67 depending on when you sign up, plus processing and event-management fees. Register on RunSignup.
Route: Variable; typically along Smathers Beach or Truman Waterfront with sunset finish.
Other Signature Events
Welcome Happy Hour at Hemingway Distillery — Papa’s Pilar rum tasting kickoff.
Key West Cooking School Hemingway-themed Dinner — Thursday evening. Multi-course meal with Hemingway-inspired dishes (often involving Papa’s Pilar rum). Ticketed $75-150.
Beach ‘N Beer Mile — Held at Southernmost Beach Café. Beer-distance hybrid run.
Closing Pool Party — Blue Flamingo Resort. Saturday evening.
Papa’s Pilar Cocktail Classic — Bartenders craft Hemingway-inspired drinks competing for prizes. Public tasting tickets often available.
Sunset Salute — Closing ceremony at Sloppy Joe’s or Mallory Square. Free.
Marina/Sloppy Joe’s celebrations — Daily happy hours at Sloppy Joe’s all week with Hemingway-themed drink specials.
Free vs Ticketed Events
FREE:
- Look-Alike Contest viewing at Sloppy Joe’s (no cover)
- Running of the Bulls (street parade)
- Caribbean Street Fair
- Sunset Salute closing ceremony
- Welcome Happy Hour at Hemingway Distillery
- Marlin Tournament weigh-in viewing
TICKETED:
- Cooking School Hemingway dinner ($75-150)
- Hemingway 5K Sunset Run registration ($46 to $67, plus fees)
- Marlin Tournament entry (boat-based)
- Papa’s Pilar Cocktail Classic public tasting (~$30-50)
Where to Watch the Look-Alike Contest
Sloppy Joe’s Bar (201 Duval Street, corner of Greene). The bar packs to capacity during preliminary nights — especially the final night.
Best viewing spots:
Inside the bar: There is no reserved seating, and hundreds of people pack in, so spectators start claiming spots in the early afternoon.
Outside on Duval: Standing on the sidewalk with a clear view through the open Sloppy Joe’s front. Free, less crowded inside, easier to come and go.
Drinks: Sloppy Joe’s serves food and drinks throughout the contest. Sloppy Joe Rum Punch ($12) is the iconic order.
Family-friendly: The contest itself is PG. The bar atmosphere skews adult, so call Sloppy Joe’s before bringing children to ask about minors on contest nights.
Hotel Strategy for Hemingway Days Week
Festival week brings crowds into Old Town, so get quotes for your exact dates early and compare a few hotels before you commit.
Book 6-9 months ahead for peak in-Old-Town hotels. Last-minute bookings during Hemingway Days week often default to Roosevelt Boulevard chain hotels or Marathon (50 miles up).
Pricing during the week:
Casa Marina: $700-1,200/night.
The Marquesa: $500-800/night.
Margaritaville Beach House: $500-800/night.
Roosevelt Boulevard chains (Hampton Inn, etc.): $300-500/night.
NYAH Key West: $200-350/night for hostel beds.
Best location: Walking distance to Sloppy Joe’s at 201 Duval Street. The Marquesa, Gardens Hotel, Eden House, and Cypress House are all in Old Town within that range.
Parking Strategy
Old Town parking during Hemingway Days is brutal. Sloppy Joe’s nights especially.
Best moves:
Park at your hotel for the duration ($35-50/night).
Walk everywhere — Old Town is one square mile.
Use Uber/Lyft for non-walking-distance moves (Marina, Truman Waterfront), and check the fare the app quotes before you confirm.
The $2 Key West Rides on-demand shuttle is another option; check the City of Key West’s Key West Rides page for service notices during the festival.
Park-and-Ride at Caroline & Grinnell with city bus.
Drive-don’t options: avoid driving into Old Town between 5 PM and midnight during the festival week.
Can Anyone Enter the Look-Alike Contest?
Yes. The Papa Hemingway Look-Alike Contest is open to anyone meeting the requirements:
- Male (the current entry form sets out the rest of the eligibility rules).
- White or grey hair (or be willing to commit to the look).
- Beard.
- Hemingway-era clothing.
- General physical resemblance.
Reality check: Veterans dominate. Many “Papas” have competed for years and have built specific costumes, mannerisms, and presentation. First-time entrants rarely win but are welcomed and often build into long-running participation. Sign-up usually happens at Sloppy Joe’s during the festival.
Entry fee: Typically free or nominal ($10-25). Confirm at Sloppy Joe’s.
Sample 4-Day Hemingway Days Itinerary
Day 1 (Arrival):
Check into hotel. Lunch at Cuban Coffee Queen. Walk Old Town. Welcome Happy Hour at Hemingway Distillery (free or $5-10 tasting). Dinner at Blue Heaven. Evening Look-Alike Contest sign-ups at Sloppy Joe’s if interested.
Day 2:
Morning at Hemingway Home (book early to beat festival crowds). Lunch at Hogfish on Stock Island. Afternoon at Higgs Beach. Evening Look-Alike Contest preliminary round 1 at Sloppy Joe’s. Late dinner.
Day 3:
Morning beach or Mel Fisher Maritime Museum. Lunch at El Siboney. Afternoon Caribbean Street Fair. Evening Look-Alike Contest preliminary round 2 at Sloppy Joe’s (arrive early). Late dinner.
Day 4:
Hemingway 5K Sunset Run if registered. Look-Alike Contest final at Sloppy Joe’s in the evening (the headline event — arrive early). Sunset Salute closing ceremony. Final Cuban dinner at El Meson de Pepe.
Photography Notes
The Look-Alike Contest, Running of the Bulls, and Caribbean Street Fair are highly photographable. The Look-Alike Society members are accustomed to being photographed — most welcome it.
Tips:
Burst mode for stage shots at the Look-Alike Contest.
Wide-angle lens for the Running of the Bulls parade.
Bring a hat and water — July sun is intense.
Tip $1-5 for posed photos with individual Look-Alikes who clearly post for the camera.
What to Wear
For festival attendance: Resort-casual, light cotton or linen. July is hot and humid (highs around 90-91°F; average relative humidity runs about 76% in the morning and 67% in the afternoon).
For Look-Alike Contest viewing: Inside Sloppy Joe’s gets crowded and warm. Wear light layers; expect to sweat.
If competing: Hemingway-era safari/fishing wear. Khaki shorts, white guayabera or cotton shirt, fishing vest, hat (no baseball cap), beard.
Frequently Asked Questions
When is Hemingway Days in Key West 2027?
July 20-25, 2027 (46th Annual). Coincides with Hemingway’s birthday July 21, 1899.
How much does it cost to attend Hemingway Days?
Free to attend most events including the Look-Alike Contest viewing, Running of the Bulls, Caribbean Street Fair, and Sunset Salute. Ticketed events include the Cooking School dinner and Hemingway 5K Sunset Run registration ($46 to $67 depending on when you register, plus fees); check each organizer’s booking page for current prices. Plus food, drinks, and accommodation costs.
Where is the Hemingway Look-Alike Contest held?
Sloppy Joe’s Bar, 201 Duval Street at the corner of Greene Street, Key West.
Can anyone enter the Hemingway Look-Alike Contest?
Yes — contestants are judged on resemblance, stage presence and character, and younger Hemingway portrayals can compete (a Young Hemingway won in 2026). Check the current entry form for eligibility. Entry fee nominal or free. Veterans dominate but newcomers are welcomed.
What is Running of the Bulls in Key West?
A Key West parody of the Pamplona Running of the Bulls. Hemingway Look-Alikes parade through downtown pushing life-size fake bulls on wheels — significantly safer than the original.
How many Hemingway look-alikes participate?
The 2026 contest had 134 registered contestants. Returning Papas from the Hemingway Look-Alike Society compete alongside first-timers.
Where do Hemingway look-alikes stay in Key West?
Walking distance to Sloppy Joe’s is the priority, and Old Town inns such as the Marquesa, Gardens Hotel, Cypress House and Eden House fit the bill.
Is the Look-Alike Contest family-friendly?
The contest itself is PG. Sloppy Joe’s atmosphere skews adult; ask the bar about its rules for minors before you bring kids. Children should not be in the late-night festival crowds on Duval.
When is the Lorian Hemingway Short Story Competition?
The competition runs year-round (submissions accepted June through May). Winners are announced and read their stories during Hemingway Days each July.
How long is Hemingway Days?
The festival runs 5-6 days, with most major events concentrated Thursday through Saturday. The 2027 dates are July 20-25.
What is the Hemingway Look-Alike Society?
A fellowship of past and current Look-Alike Contest participants. The Society funds scholarship programs and other charitable causes. Membership requires having competed at the Hemingway Days Look-Alike Contest.
Do hotels sell out for Hemingway Days?
Check availability for your exact festival dates early, starting with the Old Town hotels near Sloppy Joe’s. Last-minute bookings during festival week often default to Marathon (50 miles up).
Final Thoughts
Hemingway Days is one of America’s most distinctive small-town festivals — five days of bearded white-haired Papas, costume parades, literary readings, and offshore fishing tournaments centered on a single Sloppy Joe’s bar. For Hemingway fans, literary buffs, or just travelers wanting a uniquely Key West week, the festival is worth the planning. Book hotels early, build your week around the Look-Alike Contest final, walk everywhere in Old Town, and bring a camera. The Papas come back every July, and the 46th edition, July 20-25, 2027, is one you’ll want to see in person.
For more on planning, see our complete Key West events and festivals pillar guide, our Hemingway House visitor guide, our Duval Street bars guide, our best time to visit guide, and our where to stay guide.
Hemingway Days lands in the hottest stretch of the Key West year, with highs around 90-91°F, warm nights around 80°F and the showers and thunderstorms of the June-to-October wet season. Plan the daytime around the water and save your energy for the evenings at Sloppy Joe’s. Our Key West in July guide covers the weather, the Fourth of July and lobster mini-season at the end of the month.
Sources & corrections
Rates, hours and closures verified against operator listings and on-island visits. Prices are peak-season unless noted.
