Key West Events

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Key West Food & Wine Festival
Key West Food & Wine Festival
Jan 26 – Feb 2 all-day
Key West Food & Wine Festival @ Key West | Florida | United States
Key West Food & Wine Festival is an event where all of the top chefs and restaurants in Key West Top chefs a display culinary creativity and the Keys’ indigenous cuisine in a flavorful schedule …

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Mile 0 Fest Key West
Mile 0 Fest Key West @ Mile 0 Fest Key West
Jan 28 – Feb 1 all-day
Mile 0 Fest Key West @ Mile 0 Fest Key West | Key West | Florida | United States
Mile 0 Fest Key West is a “must see” music festival in the burgeoning Red Dirt & Americana music scene. Take in big shows at Truman Waterfront Park Amphitheatre, a state-of-the-art facility located blocks off …

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Cuda Bowl – Key West Fishing Tournament
Cuda Bowl – Key West Fishing Tournament @ Hurricane Hole Marina
Jan 31 – Feb 1 all-day
Cudu Bowl is an annual Key West fishing tournament. Shallow water flats anglers and guides are invited to hook-up and fight their barracuda rivals. Event is to be headquartered at Hurricane Hole Marina, Stock Island. …

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LaTeDa presents: Christopher Peterson’s EyeCons Cabaret 8:00 pm
LaTeDa presents: Christopher Peterson’s EyeCons Cabaret
Feb 3 @ 8:00 pm – Apr 28 @ 10:00 pm
Jan 22, 2020 – Apr 28, 2020 Location: Key West Category: Arts & Culture LaTeDa presents: Christopher Peterson’s EyeCons Cabaret Website Christopher Peterson is a master of impersonations, both visually and vocally, and his comic …

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The Studios of Key West presents: Prime Time 8:00 pm
The Studios of Key West presents: Prime Time
Feb 3 @ 8:00 pm – Feb 8 @ 10:00 pm
Jan 28, 2020 – Feb 8, 2020 Location: Key West Category: Arts & Culture The Studios of Key West presents: Prime Time This new musical follows a female TV executive in the 1970s fighting to …

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LaTeDa presents: Randy Roberts Live!
LaTeDa presents: Randy Roberts Live!
Feb 3 – Apr 24 all-day
Jan 21, 2020 – Apr 24, 2020 Location: Key West Category: Arts & Culture LaTeDa presents: Randy Roberts Live! Website The Randy Roberts Show is an all live, multi-media tribute to some of the world’s …

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Maryland and Florida Anglers Take Top Honors in Florida Keys’ Cuda Bowl 12:48 pm
Maryland and Florida Anglers Take Top Honors in Florida Keys’ Cuda Bowl
Feb 3 @ 12:48 pm – 1:48 pm
Travis Katski of Harwood, Maryland, released 172.75 inches of barracuda to win the fly division of the 2020 Cuda Bowl Tournament that ended Feb. 1 in the Lower Florida Keys. Guided by Captain Mike Odell …

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Tennessee Williams Birthday Celebration to Honor Playwright in Key West 1:59 pm
Tennessee Williams Birthday Celebration to Honor Playwright in Key West
Feb 4 @ 1:59 pm – 2:59 pm
For more than 30 years internationally renowned playwright Tennessee Williams lived and wrote theatrical masterpieces in Key West. Fans can celebrate his extraordinary talent and life with a series of cultural events scheduled Feb. 22 …

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Klass Kings Band at Sloppy Joe’s Bar 10:00 pm
Klass Kings Band at Sloppy Joe’s Bar
Feb 5 @ 10:00 pm – 10:00 pm
Klass Kings Band at Sloppy Joe’s Bar Klass Kings on stage 10:00 pm-2:00 am.  More information click here. High energy rock with a heart pumping performance! Hattiesburg, MS
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Cow Key Channel Bridge Run Entrants to Vie for Victory in ‘Zero K’ Race 11:37 am
Cow Key Channel Bridge Run Entrants to Vie for Victory in ‘Zero K’ Race
Feb 6 @ 11:37 am – 12:37 pm
The Cow Key Channel Bridge, stretching about 300 feet between Key West and neighboring Stock Island, is among the shortest of the Florida Keys Overseas Highway’s 42 bridges. Yet Saturday, Feb. 29, it will become …

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Klass Kings Band at Sloppy Joe’s Bar 10:00 pm
Klass Kings Band at Sloppy Joe’s Bar
Feb 6 @ 10:00 pm – 10:00 pm
Klass Kings Band at Sloppy Joe’s Bar Klass Kings on stage 10:00 pm-2:00 am.  More information click here. High energy rock with a heart pumping performance! Hattiesburg, MS
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First Fridays on Fleming
First Fridays on Fleming
Feb 7 all-day
First Day on Fleming – Key West boutique owners in “The Fabulous 500 Block of Fleming Street” have kicked off a monthly First Fridays on Fleming 6-9 p.m. block party to encourage local buying. First …

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Presidential Descendants to Explore Relatives’ Legacies Feb. 15 in Key West 9:55 am
Presidential Descendants to Explore Relatives’ Legacies Feb. 15 in Key West
Feb 7 @ 9:55 am – 10:55 am
Descendants of former presidents Harry S. Truman, Dwight D. Eisenhower, Theodore Roosevelt and William McKinley are to discuss their famous relatives’ lives and legacies Saturday, Feb. 15, at Key West’s Harry S. Truman Little White …

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Klass Kings Band at Sloppy Joe’s Bar 10:00 pm
Klass Kings Band at Sloppy Joe’s Bar
Feb 7 @ 10:00 pm – 10:00 pm
Klass Kings Band at Sloppy Joe’s Bar Klass Kings on stage 10:00 pm-2:00 am.  More information click here. High energy rock with a heart pumping performance! Hattiesburg, MS
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Klass Kings Band at Sloppy Joe’s Bar 10:00 pm
Klass Kings Band at Sloppy Joe’s Bar
Feb 8 @ 10:00 pm – 10:00 pm
Klass Kings Band at Sloppy Joe’s Bar Klass Kings on stage 10:00 pm-2:00 am.  More information click here. High energy rock with a heart pumping performance! Hattiesburg, MS
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Key West Artisan Market: Love is in the Air Edition
Key West Artisan Market: Love is in the Air Edition
Feb 9 all-day
Feb 9, 2020 Location: Key West Key West Artisan Market: Love is in the Air Edition Find everything you need for your sweeties including wine & champagne by the bottle, beautiful jewelry, gifts and all …

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Klass Kings Band at Sloppy Joe’s Bar 10:00 pm
Klass Kings Band at Sloppy Joe’s Bar
Feb 9 @ 10:00 pm – 10:00 pm
Klass Kings Band at Sloppy Joe’s Bar Klass Kings on stage 10:00 pm-2:00 am.  More information click here. High energy rock with a heart pumping performance! Hattiesburg, MS
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‘Conch Honkers’ to Vie for Victory in Key West March 7 12:52 pm
‘Conch Honkers’ to Vie for Victory in Key West March 7
Feb 10 @ 12:52 pm – 1:52 pm
It’s not a stringed instrument, a percussion instrument or the musical choice of virtually any “American Idol” contestant. Nonetheless, the conch shell takes center stage in Key West’s music scene each spring, when several dozen …

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Klass Kings Band at Sloppy Joe’s Bar 10:00 pm
Klass Kings Band at Sloppy Joe’s Bar
Feb 10 @ 10:00 pm – 10:00 pm
Klass Kings Band at Sloppy Joe’s Bar Klass Kings on stage 10:00 pm-2:00 am.  More information click here. High energy rock with a heart pumping performance! Hattiesburg, MS
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Fresh Seafood and Family Fun Highlight Original Marathon Seafood Festival March 14-15 2:46 pm
Fresh Seafood and Family Fun Highlight Original Marathon Seafood Festival March 14-15
Feb 11 @ 2:46 pm – 3:46 pm
Shrimp, spiny lobster, stone crab claws and fish, all “fishermen-to-fork fresh,” are to headline the attractions for attendees at the Original Marathon Seafood Festival scheduled Saturday and Sunday, March 14-15, in Marathon.N
Klass Kings Band at Sloppy Joe’s Bar 10:00 pm
Klass Kings Band at Sloppy Joe’s Bar
Feb 11 @ 10:00 pm – 10:00 pm
Klass Kings Band at Sloppy Joe’s Bar Klass Kings on stage 10:00 pm-2:00 am.  More information click here. High energy rock with a heart pumping performance! Hattiesburg, MS
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Waterfront Playhouse presents: Lady Day at Emerson’s Bar and Grill 7:00 pm
Waterfront Playhouse presents: Lady Day at Emerson’s Bar and Grill
Feb 12 @ 7:00 pm – Feb 15 @ 10:30 pm
Feb 12, 2020 – Feb 15, 2020 Location: Key West Category: Arts & Culture Waterfront Playhouse presents: Lady Day at Emerson’s Bar and Grill The time is 1959. The place is a seedy bar in …

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Contest Prize Is a Fishing Vacation to Northernmost and Southernmost Points in the U.S. 2:56 pm
Contest Prize Is a Fishing Vacation to Northernmost and Southernmost Points in the U.S.
Feb 12 @ 2:56 pm – 3:56 pm
Anglers can enter to win a two-destination vacation to fish freshwater and saltwater species in the “Northernmost to Southernmost Fishing Trip Giveaway” that spotlights recreational angling in Lake of the Woods, Minnesota, and the Florida …

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Naked Karate Girls at Sloppy Joe’s Bar 10:00 pm
Naked Karate Girls at Sloppy Joe’s Bar
Feb 12 @ 10:00 pm – 10:00 pm
Naked Karate Girls at Sloppy Joe’s Bar Naked Karate Girls website. On stage 10:00 pm to 2:00 am. The Best Band in the Galaxy! Cincinnati, OH
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Naked Karate Girls at Sloppy Joe’s Bar 10:00 pm
Naked Karate Girls at Sloppy Joe’s Bar
Feb 13 @ 10:00 pm – 10:00 pm
Naked Karate Girls at Sloppy Joe’s Bar Naked Karate Girls website. On stage 10:00 pm to 2:00 am. The Best Band in the Galaxy! Cincinnati, OH
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Sombrero Beach Run/Walk to Highlight Family Fun Weekend March 6-8 10:43 am
Sombrero Beach Run/Walk to Highlight Family Fun Weekend March 6-8
Feb 14 @ 10:43 am – 11:43 am
Florida Keys sunshine and family togetherness attract hundreds of avid runners and walkers from around the U.S. to the Middle Keys each year for the Sombrero Beach Run, a mixture of athleticism and beach fun. …

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Oh My Gods and Goddesses: A Heavenly Burlesque Show 7:30 pm
Oh My Gods and Goddesses: A Heavenly Burlesque Show
Feb 14 @ 7:30 pm – 9:30 pm
Feb 14, 2020 Location: Key West Category: Arts & Culture Oh My Gods and Goddesses: A Heavenly Burlesque Show Key West Burlesauqe presents a burlesque show of epic proportion! This ”one night only” production will …

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Tennessee Williams Theater presents: Mandy Patinkin 7:30 pm
Tennessee Williams Theater presents: Mandy Patinkin
Feb 14 @ 7:30 pm – 10:00 pm
Feb 14, 2020 Location: Key West Category: Arts & Culture Tennessee Williams Theater presents: Mandy Patinkin Mandy Patinkin in Concert: DIARIES, presents the acclaimed actor / singer / storyteller in his most electrifying role: concert …

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Oh My Gods and Goddesses: A Heavenly Burlesque Show 8:00 pm
Oh My Gods and Goddesses: A Heavenly Burlesque Show
Feb 14 @ 8:00 pm – 9:30 pm
Feb 14, 2020 Location: Key West Category: Arts & Culture Oh My Gods and Goddesses: A Heavenly Burlesque Show Key West Burlesauqe presents a burlesque show of epic proportion! This ”one night only” production will …

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Naked Karate Girls at Sloppy Joe’s Bar 10:00 pm
Naked Karate Girls at Sloppy Joe’s Bar
Feb 14 @ 10:00 pm – 10:00 pm
Naked Karate Girls at Sloppy Joe’s Bar Naked Karate Girls website. On stage 10:00 pm to 2:00 am. The Best Band in the Galaxy! Cincinnati, OH
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Naked Karate Girls at Sloppy Joe’s Bar 10:00 pm
Naked Karate Girls at Sloppy Joe’s Bar
Feb 15 @ 10:00 pm – 10:00 pm
Naked Karate Girls at Sloppy Joe’s Bar Naked Karate Girls website. On stage 10:00 pm to 2:00 am. The Best Band in the Galaxy! Cincinnati, OH
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Naked Karate Girls at Sloppy Joe’s Bar 10:00 pm
Naked Karate Girls at Sloppy Joe’s Bar
Feb 16 @ 10:00 pm – 10:00 pm
Naked Karate Girls at Sloppy Joe’s Bar Naked Karate Girls website. On stage 10:00 pm to 2:00 am. The Best Band in the Galaxy! Cincinnati, OH
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Willie Nelson At Key West Amphitheater 7:00 pm
Willie Nelson At Key West Amphitheater
Feb 17 @ 7:00 pm – 10:00 pm
Feb 17, 2020 Location: Key West Category: Arts & Culture Willie Nelson At Key West Amphitheater With a six-decade career and 200 plus albums, this iconic Texan is the creative genius behind the historic recordings …

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Naked Karate Girls at Sloppy Joe’s Bar 10:00 pm
Naked Karate Girls at Sloppy Joe’s Bar
Feb 17 @ 10:00 pm – 10:00 pm
Naked Karate Girls at Sloppy Joe’s Bar Naked Karate Girls website. On stage 10:00 pm to 2:00 am. The Best Band in the Galaxy! Cincinnati, OH
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Divers to Take a Bite Out of Lionfish at Key Largo Derby April 3-4 10:38 am
Divers to Take a Bite Out of Lionfish at Key Largo Derby April 3-4
Feb 18 @ 10:38 am – 11:38 am
Divers are to convene in Key Largo Friday and Saturday, April 3-4, for the Reef Environmental Education Foundation’s 2020 Winter Lionfish Derby Series in the Florida Keys.N
Naked Karate Girls at Sloppy Joe’s Bar 10:00 pm
Naked Karate Girls at Sloppy Joe’s Bar
Feb 18 @ 10:00 pm – 10:00 pm
Naked Karate Girls at Sloppy Joe’s Bar Naked Karate Girls website. On stage 10:00 pm to 2:00 am. The Best Band in the Galaxy! Cincinnati, OH
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Florida Keys Ocean Fest to Celebrate Marine World March 28 11:32 am
Florida Keys Ocean Fest to Celebrate Marine World March 28
Feb 19 @ 11:32 am – 12:32 pm
The vibrant marine environment of the continental United States’ southernmost island chain is to be celebrated Saturday, March 28, with live music, art, activities for kids, educational exhibits and more during Mote Marine Laboratory’s Ocean …

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Florida Keys’ Little Palm Island Resort & Spa to Reopen March 1 12:22 pm
Florida Keys’ Little Palm Island Resort & Spa to Reopen March 1
Feb 19 @ 12:22 pm – 1:22 pm
Little Palm Island Resort & Spa is scheduled for a soft reopening March 1, almost two and one-half years after Hurricane Irma ravaged the 4-acre island off Little Torch Key in the Lower Florida Keys, …

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The Studios of Key West presents: Anna in the TropicsWebsite 8:00 pm
The Studios of Key West presents: Anna in the TropicsWebsite
Feb 19 @ 8:00 pm – 10:00 pm
Feb 19, 2020 – Feb 29, 2020 Location: Key West Category: Arts & Culture The Studios of Key West presents: Anna in the Tropics Website: https://tskw.org/anna-in-the-tropics/ In Nilo Cruz’s Pulitzer Prize winning script, Juan Julian …

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Live Music to Rock at Islamorada’s Daylong ‘Bay Jam 26’ April 5 9:24 am
Live Music to Rock at Islamorada’s Daylong ‘Bay Jam 26’ April 5
Feb 21 @ 9:24 am – 10:24 am
Live musical performers representing Americana, blues, rock, funk and other genres are to entertain audiences from midday into the evening Sunday, April 5, at Islamorada’s Bay Jam 26.N
Clinton Curry: Steward of Key West’s Heritage 9:41 am
Clinton Curry: Steward of Key West’s Heritage
Feb 21 @ 9:41 am – 10:41 am
Clinton Curry is a seventh-generation Key West resident or “Conch” whose ancestors arrived some 180 years ago from the Bahamas’ Green Turtle Cay. The fifth generation of his family to be born on the island, …

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Rams Head Production presents: Kool & the Gang, with The Village People 5:30 pm
Rams Head Production presents: Kool & the Gang, with The Village People
Feb 21 @ 5:30 pm – 10:00 pm
Feb 21, 2020 Location: Key West Category: Arts & Culture Rams Head Production presents: Kool & the Gang, with The Village People From Nairobi to Newark, Kool & the Gang has performed continuously longer than …

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55th Annual Old Island Days Art Festival
55th Annual Old Island Days Art Festival
Feb 22 all-day
Feb 22, 2020 – Feb 23, 2020 Location: Key West Category: Arts & Culture 55th Annual Old Island Days Art Festival 304-294-1243 Website: https://keywestartcenter.com/ The 55th annual juried outdoor fine art festival features over 70 …

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Impromptu Classical Concerts presents: The Rascher Saxophone Quartet 4:00 pm
Impromptu Classical Concerts presents: The Rascher Saxophone Quartet
Feb 23 @ 4:00 pm – 5:30 pm
Feb 23, 2020 Location: Key West Category: Arts & Culture Impromptu Classical Concerts presents: The Rascher Saxophone Quartet Website: http://www.keywestimpromptu.org/concerts/season/2020-season The Raschèr Saxophone Quartet appears regularly at major concert halls in Europe, Asia and the …

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Drunken Spelling Bee Contest @ Mary Ellen’s Bar Monday Nights at 9 PM! 9:00 pm
Drunken Spelling Bee Contest @ Mary Ellen’s Bar Monday Nights at 9 PM!
Feb 24 @ 9:00 pm – 11:00 pm
Drunken Spelling Bee Contest @ Mary Ellen’s BarMonday Nights at 9 PM!Hosted by Comedy Key West’s Joe Madaus, Tony Hughes, and Steve Crane.Shot rounds, speed rounds and we don’t even know what else yet. It will …

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Wednesdays! The MadHouse at Bottlecap 7:30 pm
Wednesdays! The MadHouse at Bottlecap
Feb 26 @ 7:30 pm – 10:00 pm
Wednesdays!The MadHouse at BottlecapEnjoy comedy, variety, and impropriety featuring local “open mic” standup & who knows what else… Bring your own talent and you might be part of the show! If you’re interested in performing, …

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Sixth Annual Cow Key Channel Bridge Run 10:00 am
Sixth Annual Cow Key Channel Bridge Run
Feb 29 @ 10:00 am – 2:00 pm
Feb 29, 2020 Location: Key West Sixth Annual Cow Key Channel Bridge Run Website: http://cowkeybridgerun.com/ Feel like running across a bridge in the Florida Keys without waking up early or breaking a sweat? From 10AM …

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LaTeDa presents: Randy Roberts Live!
LaTeDa presents: Randy Roberts Live!
Feb 5 all-day
Jan 21, 2020 – Apr 24, 2020 Location: Key West Category: Arts & Culture LaTeDa presents: Randy Roberts Live! Website The Randy Roberts Show is an all live, multi-media tribute to some of the world’s …

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12:00 am LaTeDa presents: Christopher Peterson’s EyeCons Cabaret
LaTeDa presents: Christopher Peterson’s EyeCons Cabaret
Feb 5 @ 12:00 am – Feb 6 @ 12:00 am
Jan 22, 2020 – Apr 28, 2020 Location: Key West Category: Arts & Culture LaTeDa presents: Christopher Peterson’s EyeCons Cabaret Website Christopher Peterson is a master of impersonations, both visually and vocally, and his comic …

LaTeDa presents: Christopher Peterson’s EyeCons Cabaret Read More »

12:00 am The Studios of Key West presents: Prime Time
The Studios of Key West presents: Prime Time
Feb 5 @ 12:00 am – Feb 6 @ 12:00 am
Jan 28, 2020 – Feb 8, 2020 Location: Key West Category: Arts & Culture The Studios of Key West presents: Prime Time This new musical follows a female TV executive in the 1970s fighting to …

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10:00 pm Klass Kings Band at Sloppy Joe’s Bar
Klass Kings Band at Sloppy Joe’s Bar
Feb 5 @ 10:00 pm – 10:00 pm
Klass Kings Band at Sloppy Joe’s Bar Klass Kings on stage 10:00 pm-2:00 am.  More information click here. High energy rock with a heart pumping performance! Hattiesburg, MS