Events

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! Dancing starts at 5:30pm The Prime Movers, then Turning The Tide on stage following the contest, plus our house DJ will keep you dancing all night. To enter the costume contest sign up next to stage at 8:15pm, contest on stage at 9:00pm. You may enter the contest as an individual or as a group of 2-4 people (must be in costume). Prizes: 1st place $500 Sloppy Joe’s Gift Card; 2nd place $250 Sloppy Joe’s Gift Card; and third place $100 Sloppy Joe’s Gift Card. Other giveaways throughout the night.

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”
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? Create your outfit around Fantasy Fest Theme “It’s a 90’s Neon Cosmic Carnival” (a costume you can wear all week). Don’t hit the snooze button, the party starts at 5:30pm with Rock House on stage. To enter the costume contest sign up next to stage at 8:15pm, contest on stage at 9:00pm. You may enter the contest as an individual or as a group of 2-4 people (must be in costume). Spend the day and night partying and dancing in comfort at Sloppy Joe’s. Prizes: 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. Other giveaways throughout the night.

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!” Wear a traditional ancient Toga or dare to create your Toga using Fantasy Fest theme “It’s a 90’s Neon Cosmic Carnival” Live music on stage all day! Dancing starts at 5:30pm Rock House and then Laura Lea & Tripp Fabulous on stage after the Toga contest, plus our house DJ makes the party happen all night. Sign up for Toga Contest 8:15pm, contest on stage at 9:00pm. You may enter the contest as an individual or as a group (a group is a minimum of 2 people and maximum of 4 people) must be in Toga(s). Prizes: 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. Other giveaways throughout the night.

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.

November 2024

Saturday, November 2, 2024

Sloppy Joe’s celebrates Dia De Los Muertos “Day of the Dead” 
Celebrate all day at Sloppy Joe’s with a vibrant Día de los Muertos celebration filled with artistry and community spirit! Celebrate life, honor loved ones, and give back with a day of live entertainment, face painting and fiesta.  Face Painters will be on site for hand-painted sugar skull designs and more. Creative costume prizes throughout the day.  Flower Crowns and Cat Ears available for a donation to Sloppy Joe’s Foundation which gives back to our Key West Community.  Customers may also give donations on behalf of their favorite employee to vote for the people’s choice “best staff costume.”

Entertainment:

• 10:00am-11:45 am  |  El Jefe
• 12:00pm-4:45pm  |  Coco El Mariachi
• 5:30pm-9:30pm  |  Behind Bootleg
• 10:00pm  |  Rock House

December 2024

December 1-5, 2024 “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 Key West End of Prohibition Celebration event website at https://KeyWestBootleggers.com.

Sunday, December 1, 2024
Countdown to Key West End of Prohibition Celebration begins – Sloppy Joe’s 201 Duval Street
Sloppy Joe’s Blonde Reserve Rum Anniversary
Live Entertainment 10:00am-2:00am

Monday, December 2, 2024
Mixology Presentation more information to come
Live Entertainment 10:00am-2:00am

Tuesday, December 3, 2024
Key West End of Prohibition Celebration at Sloppy Joe’s
Live Entertainment 10:00am-2:00am

Wednesday, December 4, 2024
Key West End of Prohibition Celebration at Sloppy Joe’s
Live Entertainment 10:00am-2:00am

Thursday, December 5, 2024
Key West End of Prohibition Celebration at Sloppy Joe’s
Party like it’s 1933! End of Prohibition 91st Anniversary! All Day Celebration with host Landon Bradbary. Costume & Best Dressed contests, Good Times, Great Drinks, Giveaways. Special Appearance Anhueser-Busch’s Antique Truck. Don’t miss the 5 o’clock hour Repeal festivities.
Live Entertainment 10:00am-2:00am

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.

Photo by Carol Tedesco