Sloppy Joe’s Key West Events Calendar
October 2026
October 16-25, 2026
Fantasy Fest
October 16 – 25, 2026
Sloppy Joe’s Hangover Hospital
Hungover? We have the cure! Head to Sloppy Joe’s Bar…Your Hangover Headquarters! Our perfect remedies include Deep Eddy Vodka Cocktails, Dulce Vida Frozen Margaritas, Bloody Mary’s, live entertainment & fun throughout the morning. Let the cold drinks, air conditioning & live music ease you back to the festivities. The kitchen opens at 10am to help fuel the day. Whether you are nursing your glitter-covered self in sunglasses or dressed for the next party, you will fit right in! Skip the morning-after regret and let us be your Hangover Heroes. Trust us, this is one hangover cure you’ll want to remember! All week long 9am – RECOVERY! Sloppy Joe’s 201 Duval Street. #STILLTHEBESTPARTYINTOWN
Sunday, October 18, 2026
Sloppy Joe’s Monster Bash & Graveyard Groove Dance Party
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- 5:30pm Audio Graffiti
- 10:00pm Radio Hero
Live Broadcast of Zombie Bike Ride to the SloppyTron, Facebook & Website
Monday, October 19, 2026
Sloppy Joe’s Comic Book Cape-ers Party
Are you a Superhero or Supervillain? Dress as your favorite “Caped Crusader” or “Villainous Vixen” & party day to night with live music starting at 10am! Enter our 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. Sign up begins at 8:15pm next to the stage with the contest starting at 9:00pm. Enter the contest as an individual or group of 2-4 people (must be in costume). “Radio Hero” takes the Sloppy’s Stage following the contest to keep you dancing all night long! Sloppy Joe’s 201 Duval Street. #STILLTHEBESTPARTYINTOWN
Wednesday, October 21, 2026
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).
Thursday, October 22, 2026
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
Thursday through Saturday, December 3-5, 2026
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.
Thursday, December 31, 2026
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.
