Sloppy Joe's | Events
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December 2018

December 5, 2018 – End of Prohibition Party

Sloppy Joe’s Bar will celebrate eighty five years since the End of Prohibition.

photo by Johnny White 









December 2018

December 31, 2018

NEW YEARS EVE — Sloppy Joe’s 26th Annual Dropping of the Conch Shell

Sloppy Joe’s will host its 26th Annual Dropping of the Conch Shell. Any thing goes New Year’s Eve in Key West on Duval Street. You’ll find people all decked out for the midnight celebration, and folks still in their bathing suits and flip flops when the Conch Shell drops from the roof of Sloppy Joe’s Bar.

The idea and implementation of the New Year’s Eve Dropping of the Conch Shell is that of local artist Tobias McGregor. In 1993, McGregor approached Sloppy Joe’s management about the New Year’s Eve plan. “Before the dropping of the Conch Shell, everyone would just wonder around Duval Street, celebrating the New Year when their watches read midnight. The crowd was just not in sync,” said McGregor.

The initial Conch Shell was rigged on a frame, the shell was lowered manually, and timed by watch, or by looking across the street into a window and watching the countdown in Times Square on someone’s TV. McGregor said, “the Queen Conch has come a long way since the early years, and the crowd at the corner of Duval and Greene expects more each year.”

Outside the crowd starts to gather on the street around 10:00pm as Sloppy Joe’s rooftop host entertains the crowd and everyone dances, catches beads and waits for the countdown clock to begin. As midnight strikes and the Conch Shell is lowered confetti, streamers and lights will fill the sky.

No reservations taken. No tickets sold.

New Years Eve 2017 photo Carol Tedesco


February 2019

Sloppy Joe’s 15th Annual Put-In-Bay Music Festival February 6-9, 2019.

Schedule to come.

May 2019

May 5, 2019 Sloppy Joe’s celebrates 82 years at the corner of Duval and Greene.


July 2019

Sloppy Joe’s 39th Annual Hemingway® Look-Alike Contest July 18-21, 2019.   For more information visit our Hemingway® Look-Alike page.


5:30 p.m.- -Meet the “Papas.” Get to know the contestants and previous winners of Sloppy Joe’s Hemingway® Look-Alike Contest.  AT SLOPPY JOE’S. 


5:00 p.m. – Thursday night contestants need to check in at registration table.

6:00 p.m. – Hemingway Look-Alike Society scholarship presentations. The society is to announce the winners of its annual scholarships for Florida Keys students. On stage at Sloppy Joe’s Bar. 

6:30 p.m. – Sloppy Joe’s 39th Annual Hemingway® Look-Alike Contest – Preliminary Round One on stage at Sloppy Joe’s Bar.


5:00 p.m. – Friday night contestants need to check in at registration table.

6:30 p.m. – Sloppy Joe’s 39th Annual Hemingway® Look-Alike Contest – Preliminary Round Two on stage at Sloppy Joe’s Bar.


Noon – Photos with “Papas.” Hemingway® Look-Alikes provide a photo opportunity for fans. Greene Street outside Sloppy Joe’s. 

 1:00 p.m. – Running of the Bulls. This wacky event is sponsored by Sloppy Joe’s Bar and features past Hemingway® Look-Alike Contest winners dressed in their Pamplona best — and a breed of “bull” found only in Key West.  The fun takes place on Greene street outside Sloppy Joe’s. 

HLAS will sell red berets and red bandanas (limited quantities) beginning at 12 Noon on Saturdays.  Those wishing to wear tradition white clothing with red sash need to be prepared and bring their own clothing (these items not sold).

 6:30 p.m. – Sloppy Joe’s 39th Annual Hemingway® Look-Alike Contest – FINALS to name Papa 2019.


10:00am – Bloody Mary’s with Papa

Sloppy Joe’s Arm Wrestling Championship.  Prizes await winners in multiple weight categories. Sloppy Joe’s. $5 entry fee; free to watch.  Registration at 10:00am contest at 11:00am  (must register same day before 10:45am).  For info, visit[].


October 2019

October 20, 2019  Sloppy Joe’s Zombie Dance Party

Sloppy Joe’s is an official sponsor of Zombie Bike Ride.  Sloppy Joe’s Zombie Dance Party

Time:  7:00 pm to close

Sloppy Joe’s Gift Cards will be awarded after 9:30 pm for best Zombie costumes. 


October 21, 2019  Sloppy Joe’s Comic Book Cape-ers Party

An Official Fantasy Fest event.  

Time: 8:00 pm to close

Are you a Superhero with superhuman powers to protect the universe? Or are you the ultimate Supervillain?   Come dress as your favorite “Caped” Superhero or Supervillain and party all night.  Sloppy Joe’s gift cards will be awarded to best costumes after 9:30pm.

No door charge.

Key West Theme Runs Heroes and Villains Run/Walk 5K click here for more information.

October 24, 2019  Sloppy Joe’s Annual Toga Party

Toga! Toga! Toga! Sloppy Joe’s Toga Party is “An Original Fantasy Fest Event.” Get your toga ON and find out why we are “Still The Best Toga Party in Town!”  Transport yourself back in time with a traditional ancient Toga or dare to create your Toga using Fantasy Fest theme “In tune…but out of key. Celebrating 40 Years of Fantasy Fest.”  Best Togas will win Sloppy Joe’s gift cards throughout the night. Limited Toga sheets are available for purchase in the Sloppy Joe’s Retail Store for $10 (Proceeds to AH of Monroe County). 201 Duval Street. 8 PM. Door charge.

  • At 9:30 pm, we will have Toga Ceremony to award best Togas. Groups of 2-8 people may participate in Ceremony.  To participate in the 9:30 Toga Ceremony, groups need to sign up at table next to the stage.  Sign up will be from 8:00 pm to 9:15 pm.  Audience will choose winner. First Place $300 Sloppy Joe’s Gift Card, Second Place $200 Sloppy Joe’s Gift Card and Third Place $100 Sloppy Joe’s Gift Card. 
  • We will be having mini impromptu contests during band breaks.  Audience will choose winner.  Sloppy Joe’s Gift Card giveaways.
  • Contestants must be dressed in a toga and are encouraged to dress in Ancient Roman theme or be creative using the Fantasy Fest theme “In tune…but out of key. Celebrating 40 Years of Fantasy Fest” for their toga.  Body paint is not a toga, but may be used as part of the toga costume.


(305) 294-5717 • Open Daily 9am – 4am (Noon on Sunday)