Events
Check out Sloppy Joe’s Daily Entertainment Calendar, click here.
July 2025
Thursday, July 3, 2025 – Sloppy Joe’s Key Lime Pie Smash
Vote with Donations & Bid in our Live Auction to have some of your favorite Local Celebrities & Sloppy Joe’s Staff get a Key Lime Pie to the face! Donations to benefit the Sloppy Joe’s Foundation! Sloppy Joe’s is “Still The Best Party In Town!” 5:30pm-9:30pm
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 hemingwaydays.com .
Sloppy Joe’s 44th Hemingway® Look-Alike Contest – 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
9:00 am Bloody Mary’s with Papas at Sloppy Joe’s and Papa 126 Birthday Celebration, with cake at noon.
Papa 2024 Bat Masterson
October 2025
Sunday, October 19, 2025
Sloppy Joe’s Monster Bash & Graveyard Groove
Come dressed as your favorite zombie, monster or graveyard character. Details to come.
Monday, October 20, 2025
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. Details to come.
Tuesday, October 21, 2025
Show off your Tutu at Sloppy Joe’s.
Wednesday, October 22, 2025
Sloppy Joe’s Slumber Party Costume Contest “An Official Fantasy Fest Event”
Dreaming of the Best Party in Town? Roll out of bed and head on over to Sloppy Joe’s Slumber Party. Be creative. Be goofy. But be dressed in a Sleepwear…will it be… a onesie, flannel jammies, boxers or your favorite lingerie? Details to come.
Thursday, October 23, 2025
Sloppy Joe’s 46th 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!” Wear a traditional ancient Toga or dare to create your Toga using Fantasy Fest theme. Details to come.
Friday, October 24, 2025
Celebrate Fantasy Week with us. Live Music 10am-2:00am.
Saturday, October 25, 2025
Watch the Fantasy Fest Parade at Sloppy Joe’s. The parade will be shown on our Sloppy Tron screen.
December 2025
Saturday, December 3 through the 5th
“Key West End of Prohibition Celebration“
“Take a step back into old Key West and celebrate the end of Prohibition with five days of fun-filled Prohibition-themed Films, Cocktails, History, Live Entertainment, and, of course, a blowout Party at Sloppy Joe’s! A true celebration of not only Key West’s but America’s most iconic eras.
Don’t miss the opportunity to dust off your Flapper Dresses and Fedoras for the best Costume Party since 1933.
Visit the official Key West End of Prohibition Celebration event website at https://KeyWestBootleggers.com.
December 31, 2025
New Year’s Eve – Sloppy Joe’s 32nd Annual Dropping of the Conch Shell.
No reservations taken, tables first come basis. There is no door charge.
Inside on stage:
10:00 am-11:45 am TBA
Noon-4:45 pm TBA
5:30 pm-9:30 pm TBA
10:00 pm-2:00 am TBA
Outside live from the roof:
10:00 pm Sloppy Joe’s 32nd Annual Dropping of the Conch Shell at midnight to ring in 2026!
History: This year, the conch shell will drop for the 31st 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.
Photo by Carol Tedesco
April 2026
April dates to be announced Conch Republic Celebration
May 2026
April 29- May 2, 2026 – Key West Songwriters Festival
May 1, 2026 Key West Songwriters on stage at Sloppy Joe’s 5:30 pm-9:30 pm
scheduled to be determined
May 3, 2026 Key West Songwriters on stage at Sloppy Joe’s Noon-4:45 pm
scheduled to be determined
May 5, 2026 Sloppy Joe’s celebrates 89 years at the corner of Duval and Greene
Photo: Sloppy Joe’s Bar and Cabaret on Duval Street, Key West. The DeWolfe and Wood Collection.
