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July 2021

Sloppy Joe’s 40th Annual Hemingway® Look-Alike Contest July 22-24,2021

Look-Alike contest preliminary rounds will be July 22 & 23 at 6:30 pm inside, on stage Sloppy Joe’s Bar.  Final round will be held on stage Saturday, July 24th at 6:30pm.

Wednesday July 21st               5:00 pm Meet and Greet the Papas at Sloppy Joe’s

Thursday July 22nd                  5:00 pm contestants check in

                                                 6:00 pm scholarship presentation

                                                 6:30 pm First preliminary round

Friday July 23rd                        5:00 pm contestants check in

                                                6:30 pm Second preliminary round

Saturday, July 24th                  12:00 pm photo of with Papas and the Bulls on Greene St.

                                                   1:00 pm Running of the Bulls

                                                   5:30 pm finalists check in

                                                   6:30 pm Final round to name Papa 2021

There will be no arm wrestling on Sunday this year.

Due to Covid Sloppy Joe’s reserves the right to make changes including canceling part or all of contest events if necessary.  


October 2021

October 24, 2021 Sloppy Joe’s Zombie Dance Party

October 25, 2021 Sloppy Joe’s Comic Book Cape-ers

October 28, 2021 Sloppy Joe’s Annual Toga Party

October 30, 2021 Fantasy Fest Parade 

December 2021

December 31, 2021 New Year’s Eve – Sloppy Joe’s Annual Dropping of the Conch Shell

February 2021

Put-In-Bay Music Festival

There are many things which have made Sloppy Joe’s “A Key West Tradition.”   One of them is Sloppy Joe’s Put-in-Bay Music Fest which began February 2005.

Over the years performers have come and gone.  After 35 years of performing at Sloppy Joe’s Pat Dailey retired on February 17, 2018.  Others who graced our stage for this event were: The Pete & Wayne Show, Ray Fogg, Bob Gatewood, Alex Bevan, Pat Shepard, Allie Market, Tipsy & the Donuts, Westside Steve, Mike “Maddog” Adams, Chip Brock, Chris Logsdon, Emerson Drive, Killer Flamingos, Juliano Brothers, WPIB Radio personalities and more (sorry if we overlooked anyone).

While we have been proud to feature this event 16 times, we have made the decision to retire the event, with 2020 being our last PIB show.  Sloppy Joe’s recognizes all the work Pete Jarvis and Ray Fogg have put into this event and we thank both of them for giving us this opportunity to host the PIB Music Festival in Key West.

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