Events

Check out Sloppy Joe’s Daily Entertainment Calendar, click here.

July 2024

Mini lobster season July 24-25

August 2024

September 2024

Sunday, September 1, 2024
11:00am – 5:00 pm Joe’s Tap Room at Sloppy Joe’s Sunshine State Tap Takeover
Joe’s Tap Room will feature 10 Florida Brewed Craft Beers on tap including our own Sloppy Hoppy IPA and Island Girl Ale. Enjoy tasting flights, giveaways and Beer Bingo benefiting Key West Sunrise Rotary via the Sloppy Joe’s Foundation.

October 2024

Sunday, October 20, 2024
Sloppy Joe’s Monster Bash & Graveyard Groove
Come dressed as your favorite zombie, monster or graveyard character.

Monday, October 21, 2024
Sloppy Joe’s Comic Book Cape-ers Costume Contest “An Official Fantasy Fest Event”
Come dressed as your favorite “Caped” Superhero or Supervillain and party all day and night. Live music on stage all day! More details to come.

Tuesday, October 22, 2024
Show off your Tu-tu at Sloppy Joe’s

Wednesday, October 23, 2024
Sloppy Joe’s Slumber Party Costume Contest “An Official Fantasy Fest Event”
Roll out of bed and head on over to Sloppy Joe’s Slumber Party. Be creative. Be goofy. But be dressed in a costume…will it be… a onesie, flannel jammies, boxers or your favorite lingerie. Live music on stage all day! More details to come.

Thursday, October 24, 2024
Sloppy Joe’s 45th Annual Toga Party “An Official Fantasy Fest Event”
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!” Live music on stage all day! More details to come.

Friday, October 25, 2024
Celebrate Fantasy Week with us.  Live Music 10am-2:00am.

Saturday, October 26, 2024
Watch the Fantasy Fest Parade at Sloppy Joe’s.  The parade will be shown on our Sloppy Tron screen.

December 2024

December 1-5, 2024  End of Prohibition Celebration

More information and schedule of events to be announced. Sloppy Joe’s celebrates 91 years since the End of Prohibition.

December 31, 2024 New Year’s Eve – Sloppy Joe’s 31st Annual Dropping of the Conch Shell.

More information to follow.

This year the conch shell will drop for the 30th time at the corner of Duval and Greene Street. The idea and implementation 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 wander 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 count down in Times Square on someone’s TV.  The conch shell redesign was done by Toby in 2005.

Customers inside the bar will be able to view the dropping of the conch shell on Sloppy-Tron.

New year eve drop

Photo by Carol Tedesco

May 2025

May 2025 Key West Songwriters schedule to be announced

May 5, 2025 Sloppy Joe’s celebrates 88 years at the corner of Duval and Greene

Vintage image of sloppy joe's bar
Photo: Sloppy Joe’s Bar and Cabaret on Duval Street, Key West. The DeWolfe and Wood Collection.

July 2025

Sloppy Joe’s 44th Annual Hemingway Look-Alike Contest July 23-27, 2025
To discover more about the Hemingway Look-Alike Contest, the Hemingway Look-Alike Society auction, and other complimentary events, please visit keywestlookalikes.com 

Sloppy Joe’s 44th Hemingway® Look-Alike Contest – Tentative 2025 Schedule of Events

Wednesday, July 23, 2025
5:00pm Meet & Greet the Papas at Sloppy Joe’s

Thursday, July 24, 2025
6:30pm Look-Alike Contest – Round One

Friday, July 25, 2025
6:30pm Look-Alike Contest – Round Two

Saturday, July 26, 2025
Noon Photos with Papas
1:00pm Running of the Bulls
6:30pm Look-Alike Contest FINAL ROUND to name Papa 2025

Sunday, July 27, 2025
Time to be determined… Papa Birthday Bash