Events
May 2026
April 29- May 2 – Key West Songwriters Festival
May 1 – Key West Songwriters on stage at Sloppy Joe’s, 5:30 pm-9:30 pm
May 3 – Key West Songwriters on stage at Sloppy Joe’s Noon-4:45 pm
May 5 – 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.
July 2026
July 22-26 – Sloppy Joe’s 45th Annual Hemingway Look-Alike Contest
To discover more about the Hemingway Look-Alike Contest, the Hemingway Look-Alike Society auction, and other complimentary events, please visit KeyWestLookAlikes.com.
Wednesday, July 22 – 5:00 pm Meet & Greet the Papas at Sloppy Joe’s
Thursday, July 23 – 6:30 pm – Look-Alike Contest – Round One
Friday, July 24 – 6:30 pm – Look-Alike Contest – Round Two
Saturday, July 25
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- Noon – Photos with Papas
- 1:00 pm – Running of the Bulls
- 6:30 pm – Look-Alike Contest FINAL ROUND to name Papa 2026
Sunday, July 26 – 9:00 am Bloody Mary’s with Papas and Papa 127 Birthday Celebration, with Cake at noon.
August 2026
August 5 – 9 – Lobterfest
September 2026
September 5 – Key West Brewfest
October 2026
October 17-18 – Goombay
October 18-24 – Fantasy Fest
October 19 – Sloppy Joe’s Comic Book Cape-ers Party
October 21 – Sloppy Joe’s Slumber Party
Dreaming of the Best Party in Town? Roll out of bed & head over to Sloppy Joe’s Slumber Party! Be creative, be goofy, but be dressed in SLEEPWEAR! Will it be a onesie, flannel jammies, boxers, or your favorite lingerie? You decide. Live music starting at 10 am! Enter the costume contest & win big! 1st Place $500 Sloppy Joe’s Gift Card; 2nd Place $250 Sloppy Joe’s Gift Card; 3rd Place $100 Sloppy Joe’s Gift Card, with other giveaways throughout the night. Sign-up begins at 8:15 pm next to the stage, with the contest starting at 9:00 pm. Enter the competition as an individual or a group of 2-4 people (must be in costume).
October 22 – Sloppy Joe’s 47th Annual Toga Party
Sloppy Joe’s 47th Annual TOGA! Party “An ORIGINAL Fantasy Fest Event!” Get your TOGA! on and find out why we are “Still The Best TOGA! Party in Town!” Wear traditional ancient TOGA! or dare to create your own TOGA! using the Fantasy Fest theme. Live music starting at 10 am! Enter the costume contest & win big! 1st Place $500 Sloppy Joe’s Gift Card; 2nd Place $250 Sloppy Joe’s Gift Card; and 3rd Place $100 Sloppy Joe’s Gift Card, with other giveaways throughout the night. Sign-up begins at 8:15 pm next to the stage, with the contest starting at 9:00 pm. You may enter the competition as an individual or a group of 2-4 people (Must be in TOGA! to enter the contest).
December 2026
December 3-5 – 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.
December 31 – New Year’s Eve – Sloppy Joe’s 33rd Annual Dropping of the Conch Shell
No reservations taken; tables on a first-come, first-served basis. There is no door charge.
Outside live from the roof:
10:00 pm Sloppy Joe’s 33rd Annual Dropping of the Conch Shell at midnight to ring in 2027!
History: This year, the conch shell will drop for the 33rd time at the corner of Duval and Greene Street. The idea and implementation of the conch shell is by 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 to watch the countdown 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 see the conch shell drop on Sloppy-Tron.
