As the Jacksonville June Bug, we like to give you the best content possible and to optimize your experience with not only us – but our city.
Every month, we will release a calendar with information on known-events going on within Jacksonville. In this calendar, you’ll find live performances, live music, trivia, bingo karaoke, concerts, and much more.
It’s important to remember that although events have a set date – it’s always subject to change whether it’s postponement or simply bad weather.
Sharing this calendar with you means that we will have to maintain this post through the whole month – and luckily for you, the Jacksonville June Bug views this as it’s duty.
The Jacksonville June Bug now presents you with – May 2025 Events In Jacksonville, Florida.
May 1, 2025 – Thursday
- TRIVIA FUN @ Culhane’s Irish Pub (Atlantic Beach)
- CAT RIDGEWAY & THE TOURISTS, and Friend of A Friend @ Jack Rabbits Live
- Electronic Thursdays Presents: Lil Texas @ Myth Nightclub
- Beautiful: The Carole King Story @ Alhambra Theatre
- Fundraiser Comedy Show for PossAbilities Plus @ First Coast Comedy
- Glory Band @ Gusto A Taste Of Rome
- TEAM TRIVIA @ Lynch’s Irish Pub
- SPLIT TONE @ Lynch’s Irish Pub
- William King Music @ Disco Witch Brewing
- David Landau @ The Comedy Zone
- Trivia @ Tom and Betty’s Restaurant
- Trivia Nation Thursday @ Whiskey Jax Kitchen & Cocktails
- Country Night w/ the Cam Wheaton Band @ Colonial Oak Music Park
- Karaoke w/ Gregg “Mr. Natural” Chirico @ Arnolds Lounge
- The Space Heaters @ Prohibition Kitchen
- Pat Benatar & Neil Giraldo @ St. Augustine Amphitheater
- Trivia @ Bottlenose Brewing
- Trivia @ Falafel X Bar
- Trivia @ Green Room Brewery
- Beach Yoga @ Elizabeth Pointe Lodge
- Hoop & Holler @ Nassau County Council On Aging
- Troubadour South @ Sandbar Amelia Island
- Eric Alabiso @ Down Under Restaurant
- Soundwavz @ The Boat House
- Bingo @ American Legion 152
- Trivia @ Mocama Wildlight
May 2, 2025 – Friday
- Live Music @ Culhane’s Irish Pub (Atlantic Beach)
- Karaoke Party with DJ Guru @ Culhane’s Irish Pub (Southside)
- Music by Sade Davidson Band! @ Jerry’s Sports Grille
- Marlon Wayans @ Florida Theatre
- SMALLPOOLS – Lovetap! 10th Anniversary Tour with REC HALL, & Tana Matz @ Jack Rabbits Live
- Harry Potter and the Deathly Hallows™ – Part 2 in Concert @ Jacksonville Center for Performing Arts
- Ignite Fridays – BLACKOUT @ Myth Nightclub
- ANVIL, DON JAMIESON, MIDNITE HELLION @ Underbelly
- Beautiful: The Carole King Story @ Alhambra Theatre
- Bowlus Ricci Quintet @ Blue Jay Listening Room
- The Main Event @ First Coast Comedy
- The Blue Show: Adults-Only Improv Comedy @ First Coast Comedy
- CASSIDY LEE @ Lynch’s Irish Pub
- KRASH PARTY @ Lynch’s Irish Pub
- Pinedas Duo @ Refinery Restaurant
- Kevan Wilson Music @ Disco Witch Brewing
- David Landau @ The Comedy Zone
- Pink Paisleys @ Tom and Betty’s Restaurant
- Tyler Allen @ Pusser’s Bar and Grill
- Live Music @ Whiskey Jax Kitchen & Cocktails
- Circus @ Colonial Oak Music Park
- Contact Buzz @ Arnolds Lounge
- Good Pluck Trio @ Prohibition Kitchen
- Chillula @ Prohibition Kitchen
- Live Music by Tom and Jim! @ The Tides Oyster Co. & Grill
- Trivia @ Time Out Sports Grill
- Trivia @ MVP’s Sports Grille
- Trivia @ Legacy Ale Works
May 3, 2025 – Saturday
- Karaoke Party with DJ Guru @ Culhane’s Irish Pub (Southside)
- VyStar Free Saturdays @ MOCA
- Intocable @ Florida Theatre
- SUMMER HOOP, ALYK, GILT, & Kicklighter @ Jack Rabbits Live
- Harry Potter and the Deathly Hallows™ – Part 2 in Concert @ Jacksonville Center for Performing Arts
- Ideas of Our Time: Jax Contemporary Artist Talks @ MOCA
- City Wide High School Prom “A Night In Venice” @ Murray Hill Theatre
- Luau Party feat. JOSH LAWRENCE @ Myth Nightclub
- DEBÍ TIRAR MÁS FIESTAS | The Bad Bunny Party @ Underbelly
- Jacksonville Sharks v Iowa Barnstormers @ VyStar Veterans Memorial Arena
- Beautiful: The Carole King Story @ Alhambra Theatre
- The Main Event @ First Coast Comedy
- The Blue Show: Adults-Only Improv Comedy @ First Coast Comedy
- The Midnight Hour @ First Coast Comedy
- CASSIDY LEE @ Lynch’s Irish Pub
- BAY STREET @ Lynch’s Irish Pub
- The Beaches Green Market @ Penman Park
- Dueling Pianos @ Refinery Restaurant
- Lip Sync Shenanigans @ Disco Witch Brewing
- David Landau @ The Comedy Zone
- Darren Corlew @ Pusser’s Bar and Grill
- Live Music @ Whiskey Jax Kitchen & Cocktails
- The Road Runners @ Arnolds Lounge
- Lunar Thunder @ Prohibition Kitchen
- Live Music by Jazzy! @ The Tides Oyster Co. & Grill
May 4, 2025 – Sunday
- Illusionist Rick Thomas @ Florida Theatre
- Katie Mahan @ Friday Musicale
- STAR RAVE (The Ultimate Star Wars Themed Electronic Event) @ Myth Nightclub
- Florida Bridal & Wedding Expo @ Prime F. Osborn III Convention Center
- RED LEATHER @ Underbelly
- Beautiful: The Carole King Story @ Alhambra Theatre
- Leslie Mendelson @ Blue Jay Listening Room
- KARAOKE @ Lynch’s Irish Pub
- The Rich Guzzi Comedy Hypnosis Show @ The Comedy Zone
- Chillakaya @ Pusser’s Bar and Grill
- Shag Dancing by First Coast Shag Club @ Arnolds Lounge
- Kat Hall @ Prohibition Kitchen
- Sailor Jane meets Jallanzo the Dub Wizzard @ Prohibition Kitchen
May 5, 2025 – Monday
- Open Mic @ Culhane’s Irish Pub (Atlantic Beach)
- Dot Dot Dot @ Florida Theatre
- JULIA GULIA @ Lynch’s Irish Pub
- Jam Session with BUD @ Whitey’s Fish Camp
- Trivia @ Hibernia Pub
- Trivia @ American Legion Post
- Trivia @ The Brew Shed
- Karaoke @ The Palace Saloon
- Sam McDonald @ PJD’s
- Turtle Jam @ Green Turtle Tavern
May 6, 2025 – Tuesday
- Trivia Fun @ Culhane’s Irish Pub (Southside)
- One Night of Queen @ Florida Theatre
- Jacksonville Jumbo Shrimp vs. Syracuse Mets @ VyStar Ballpark
- Beautiful: The Carole King Story @ Alhambra Theatre
- Max Manticof @ The Comedy Zone
- BINGO @ Tom and Betty’s Restaurant
- Open Mic @ Whiskey Jax Kitchen & Cocktails
- Bar Room Dancing @ Arnolds Lounge
- Karaoke @ Callahan’s Irish Bistro
- Trivia @ Bottleneck Brewing
- Trivia @ Moon Dog Pie House
- Trivia @ The Back 40 Urban Fresh
- Trivia @ Players Grille
- Trivia @ Green Room Brewing
- Open Mic @ The Brew Shed
- Music Bingo @ Mocama-Wildlight
May 7, 2025 – Wednesday
- TRIVIA FUN @ Culhane’s Irish Pub (Atlantic Beach)
- Trivia Fun @ Culhane’s Irish Pub (Southside)
- Free Museum Nights @ MOCA
- Kenny G @ Florida Theatre
- Wayback Wednesday featuring JOEY’S VAN playing 90’s/00’s Pop Punk/Alt & Emo hits @ Jack Rabbits Live
- JSYO Major/Minor @ Jacksonville Center for Performing Arts
- Jazz in the Park with Joe Watts @ JWJ Park
- Open Mic for Musicians/Singers @ Kava and Company (San Marco)
- BROKENCYDE, BAYYMACK, THE MEDIC DROID @ Underbelly
- Jacksonville Jumbo Shrimp vs. Syracuse Mets @ VyStar Ballpark
- Beautiful: The Carole King Story @ Alhambra Theatre
- Improv Night @ Colonial Oak Music Park
- Wednesday Live @ Gusto A Taste Of Rome
- Trivia @ Disco Witch Brewing
- Best of JAX Comedy @ The Comedy Zone
- BINGO @ Tom and Betty’s Restaurant
- Karaoke Night @ Whiskey Jax Kitchen & Cocktails
- Improv Jam @ 3rd Space Improv
- Cookin in the Kitchen @ Prohibition Kitchen
- Live Music by Ivan S! @ The Tides Oyster Co. & Grill
- Trivia @ Murray Bros. Caddyshack
- Trivia @ Mossfire Grill
- Trivia @ Fore Score Golf Tavern
- Trivia @ Time Out Sports Grill
May 8, 2025 – Thursday
- TRIVIA FUN @ Culhane’s Irish Pub (Atlantic Beach)
- THE PSYCODELICS, Universal Green, & Red Magnolia @ Jack Rabbits Live
- Electronic Thursdays Presents: Manic Focus @ Myth Nightclub
- VINCENT ANTONE, S.P.O.R.E., PAPI DISCO @ Underbelly
- Jacksonville Jumbo Shrimp vs. Syracuse Mets @ VyStar Ballpark
- Beautiful: The Carole King Story @ Alhambra Theatre
- Live at Gusto Cloud 9 Band @ Gusto A Taste Of Rome
- Sip and Paint with Sassy J @ Disco Witch Brewing
- Tony Rock @ The Comedy Zone
- Trivia @ Tom and Betty’s Restaurant
- Trivia Nation Thursday @ Whiskey Jax Kitchen & Cocktails
- Country Night w/ the Cam Wheaton Band @ Colonial Oak Music Park
- Karaoke w/ Gregg “Mr. Natural” Chirico @ Arnolds Lounge
- Fly By Night @ Limelight Theater
- Afroman @ Prohibition Kitchen
- Trivia @ Bottlenose Brewing
- Trivia @ Falafel X Bar
- Trivia @ Green Room Brewery
- Trivia @ Mocama-Wildlight
- Bingo @ American Legion Post 137
May 9, 2025 – Friday
- Live Music @ Culhane’s Irish Pub (Atlantic Beach)
- Karaoke Party with DJ Guru @ Culhane’s Irish Pub (Southside)
- Music by Party Cartel! @ Jerry’s Sports Grille
- One Stoplight Town @ Artist Connection Theatre
- Jacksonville Funk Fest @ Metropolitan Park
- LAST RESORT, BEELINE, The Understudies, and Homegrown Losers @ Jack Rabbits Live
- Cirque of Ice and Fire @ Jacksonville Center for Performing Arts
- IN GLOOM Album Release @ Underbelly
- Jacksonville Jumbo Shrimp vs. Syracuse Mets @ VyStar Ballpark
- Beautiful: The Carole King Story @ Alhambra Theatre
- The Main Event @ First Coast Comedy
- Spotlight: A Showcase of Comedy Talent @ First Coast Comedy
- Moonlight Movie – Top Gun: Maverick @ Seawalk Pavilion
- 2025 Amelia Island Dance Festival @ Amelia Community Theatre
- Almost June Music @ Disco Witch Brewing
- Tony Rock @ The Comedy Zone
- Salty Dawgs @ Tom and Betty’s Restaurant
- The Good Souls @ Pusser’s Bar and Grill
- Live Music @ Whiskey Jax Kitchen & Cocktails
- Seneca Burns @ Kona Skatepark
- Cottonmouth @ Arnolds Lounge
- The Legend of Turandot @ First Coast Opera
- Fly By Night @ Limelight Theater
- Jeremy King Duo @ Prohibition Kitchen
- Paper City Hustlers @ Prohibition Kitchen
- Live Music by Becks and Somers! @ The Tides Oyster Co. & Grill
- Trivia @ Time Out Sports Grill
- Trivia @ MVP’s Sports Grille
- Trivia @ Legacy Ale Works
- Friday Wine Tasting @ Amelia Island Wine Company
- Irish Open Mic @ O’Brien’s Irish Pub
May 10, 2025 – Saturday
- Karaoke Party with DJ Guru @ Culhane’s Irish Pub (Southside)
- One Stoplight Town @ Artist Connection Theatre
- VyStar Free Saturdays @ MOCA
- Teddy Swims: I’ve Tried Everything But Therapy Tour @ Daily’s Place Amphitheater
- Word to Your Mother @ Eclipse Nightclub & Bar
- Jacksonville Dance Theatre: Weave @ Florida Theatre
- Jacksonville Funk Fest @ Metropolitan Park
- SOUTHPAW, Resistor, Thirst, Throat Chop, & Identify the Body @ Jack Rabbits Live
- Cirque of Ice and Fire @ Jacksonville Center for Performing Arts
- Vitalize Show – A Showcase of The Arts @ Murray Hill Theatre
- SHREK RAVE @ Underbelly
- Jacksonville Jumbo Shrimp vs. Syracuse Mets @ VyStar Ballpark
- Beautiful: The Carole King Story @ Alhambra Theatre
- The Main Event @ First Coast Comedy
- The Blue Show: Adults-Only Improv Comedy @ First Coast Comedy
- The Midnight Hour @ First Coast Comedy
- Last2leave Band @ Gusto A Taste Of Rome
- The Beaches Green Market @ Penman Park
- 2025 Amelia Island Dance Festival @ Amelia Community Theatre
- Tony Rock @ The Comedy Zone
- Clay County Cruzers @ Tom and Betty’s Restaurant
- Nathan Allen @ Pusser’s Bar and Grill
- Live Music @ Whiskey Jax Kitchen & Cocktails
- Glory @ Arnolds Lounge
- Fly By Night @ Limelight Theater
- Few Fellas Brass Band @ Prohibition Kitchen
- Live Music by Kevin Q! @ The Tides Oyster Co. & Grill
May 11, 2025 – Sunday
- One Stoplight Town @ Artist Connection Theatre
- Jim Henson’s Fraggle Rock @ Florida Theatre
- Jacksonville Jumbo Shrimp vs. Syracuse Mets @ VyStar Ballpark
- Dexter Jones on Saxophone @ Disco Witch Brewing
- Fly By Night @ Limelight Theater
- Soulo Lyon @ Prohibition Kitchen
May 12, 2025 – Monday
- Open Mic @ Culhane’s Irish Pub (Atlantic Beach)
- JSYO Major/Minor @ Jacksonville Center for Performing Arts
- Bodie – Murder My Ego Tour With Gracie Binion and Yung Drew @ Murray Hill Theatre
- Name That Tune with DJ Chris @ Disco Witch Brewing
- Jam Session with BUD @ Whitey’s Fish Camp
- Micah Gillium @ Prohibition Kitchen
- Trivia @ Hibernia Pub
- Trivia @ American Legion Post
- Karaoke @ The Palace Saloon
May 13, 2025 – Tuesday
- Trivia Fun @ Culhane’s Irish Pub (Southside)
- Mat Kearney @ Florida Theatre
- SAVE FERRIS, with Keep Flying, and Knives @ Jack Rabbits Live
- Fiona Cauley @ The Comedy Zone
- BINGO @ Tom and Betty’s Restaurant
- Open Mic @ Whiskey Jax Kitchen & Cocktails
- Bar Room Dancing @ Arnolds Lounge
- Karaoke @ Callahan’s Irish Bistro
- Trivia @ Bottleneck Brewing
- Trivia @ Moon Dog Pie House
- Trivia @ The Back 40 Urban Fresh
- Trivia @ Players Grille
- Trivia @ Green Room Brewing
- Music Bingo @ Mocama-Wildlight
May 14, 2025 – Wednesday
- TRIVIA FUN @ Culhane’s Irish Pub (Atlantic Beach)
- Trivia Fun @ Culhane’s Irish Pub (Southside)
- MURPHY’S LAW, TOTAL CHAOS, & Flag on Fire @ Jack Rabbits Live
- Jazz in the Park with Joe Watts @ JWJ Park
- Open Mic for Musicians/Singers @ Kava and Company (San Marco)
- Improv Night @ Colonial Oak Music Park
- Wednesday Live @ Gusto A Taste Of Rome
- Patrick Warburton @ The Comedy Zone
- BINGO @ Tom and Betty’s Restaurant
- Karaoke Night @ Whiskey Jax Kitchen & Cocktails
- Cookin in the Kitchen @ Prohibition Kitchen
- Live Music by Vinny Jacobs! @ The Tides Oyster Co. & Grill
- Trivia @ Murray Bros. Caddyshack
- Trivia @ Mossfire Grill
- Trivia @ Fore Score Golf Tavern
- Trivia @ Time Out Sports Grill
May 15, 2025 – Thursday
- TRIVIA FUN @ Culhane’s Irish Pub (Atlantic Beach)
- One Stoplight Town @ Artist Connection Theatre
- SPACED, LOST CAUSE, SECOND IMPACT @ Underbelly
- The Faze Band @ Gusto A Taste Of Rome
- Music Trivia with Kevin Carter @ Disco Witch Brewing
- Trivia @ Tom and Betty’s Restaurant
- Trivia Nation Thursday @ Whiskey Jax Kitchen & Cocktails
- Country Night w/ the Cam Wheaton Band @ Colonial Oak Music Park
- Karaoke w/ Gregg “Mr. Natural” Chirico @ Arnolds Lounge
- Fly By Night @ Limelight Theater
- Vang Durst Trio @ Prohibition Kitchen
- Michael Franti & Spearhead – Welcome To The Family Tour @ St. Augustine Amphitheater
- Trivia @ Bottlenose Brewing
- Trivia @ Falafel X Bar
- Trivia @ Green Room Brewery
May 16, 2025 – Friday
- Live Music @ Culhane’s Irish Pub (Atlantic Beach)
- Karaoke Party with DJ Guru @ Culhane’s Irish Pub (Southside)
- One Stoplight Town @ Artist Connection Theatre
- QUAIL, and guests @ Jack Rabbits Live
- Mozart’s Requiem & Double Concerto @ Jacksonville Center for Performing Arts
- JOYWAVE: Here To Perform…Spring 2025 @ Underbelly
- Forrest Frank: Child Of God Tour Part 2 @ VyStar Veterans Memorial Arena
- My Fair Lady @ Alhambra Theatre
- Randall Bramblett @ Blue Jay Listening Room
- The Main Event @ First Coast Comedy
- Comedy inspired by true stories @ First Coast Comedy
- The Pinedas Dance Band @ Gusto A Taste Of Rome
- Anniversary VIP Dance Party @ Disco Witch Brewing
- Finesse & Tisha @ The Comedy Zone
- Spektra @ Tom and Betty’s Restaurant
- Nathan Allen @ Pusser’s Bar and Grill
- Live Music @ Whiskey Jax Kitchen & Cocktails
- Last Stand @ Arnolds Lounge
- Fly By Night @ Limelight Theater
- Cortnie Fraizer @ Prohibition Kitchen
- Chris Thomas Band @ Prohibition Kitchen
- Live Music by Dave B! @ The Tides Oyster Co. & Grill
- Trivia @ Time Out Sports Grill
- Trivia @ MVP’s Sports Grille
- Trivia @ Legacy Ale Works
May 17, 2025 – Saturday
- Karaoke Party with DJ Guru @ Culhane’s Irish Pub (Southside)
- Music by Double Down!! @ Jerry’s Sports Grille
- One Stoplight Town @ Artist Connection Theatre
- VyStar Free Saturdays @ MOCA
- Florida Theatre Ball: 90’s Style @ Florida Theatre
- THE SUPERVILLAINS, Lady Ybor, and Souvineer @ Jack Rabbits Live
- Mozart’s Requiem & Double Concerto @ Jacksonville Center for Performing Arts
- Combat Night Pro Jacksonville @ Prime F. Osborn III Convention Center
- TERROR, SPIRIT WORLD, PEST CONTROL @ Underbelly
- Jacksonville Sharks v Fishers Freight @ VyStar Veterans Memorial Arena
- My Fair Lady @ Alhambra Theatre
- The Main Event @ First Coast Comedy
- The Blue Show: Adults-Only Improv Comedy @ First Coast Comedy
- The Midnight Hour @ First Coast Comedy
- Sidewalk 65 Band @ Gusto A Taste Of Rome
- The Beaches Green Market @ Penman Park
- SING DANCE & GLOW Homeschool Talent Show @ Amelia Community Theatre
- Hupp Huppman Music @ Disco Witch Brewing
- Finesse & Tisha @ The Comedy Zone
- Darren Corlew @ Pusser’s Bar and Grill
- Live Music @ Whiskey Jax Kitchen & Cocktails
- Fly By Night @ Limelight Theater
- Esh x Schief @ Prohibition Kitchen
- Dylan Scott – Country Till I Die Tour @ St. Augustine Amphitheater
- Live Music by Ivan S! @ The Tides Oyster Co. & Grill
May 18, 2025 – Sunday
- One Stoplight Town @ Artist Connection Theatre
- HOMEGROWN LOSERS, EDGEWOOD HEAVY, and guests @ Jack Rabbits Live
- HONESTAV @ Underbelly
- GUTFELD LIVE ’25 Featuring Greg Gutfeld and special guest Tom Shillue @
VyStar Veterans Memorial Arena - 904PopUp @ Seawalk Pavilion
- My Fair Lady @ Alhambra Theatre
- The Jam Showcase @ First Coast Comedy
- Sammy Obeid @ The Comedy Zone
- Chilly Rhino @ Pusser’s Bar and Grill
- Rachel Hendrix – Film Screening @ Limelight Theater
- Fly By Night @ Limelight Theater
- Pili Pili @ Prohibition Kitchen
- HAUSER – The Rebel Is Back Tour @ St. Augustine Amphitheater
May 19, 2025 – Monday
- Open Mic @ Culhane’s Irish Pub (Atlantic Beach)
- Kyran Daniel @ Blue Jay Listening Room
- Open Mic Night with Almost @ Disco Witch Brewing
- Jam Session with BUD @ Whitey’s Fish Camp
- Sam Pacetti @ Prohibition Kitchen
- Trivia @ Hibernia Pub
- Trivia @ American Legion Post
- Karaoke @ The Palace Saloon
- Trivia @ The Brew Shed
May 20, 2025 – Tuesday
- Trivia Fun @ Culhane’s Irish Pub (Southside)
- Brit Floyd @ Florida Theatre
- NUSA 50th Golden Anniversary & Annual Conference @ Prime F. Osborn III Convention Center
- Jacksonville Jumbo Shrimp vs. Memphis Redbirds @ VyStar Ballpark
- My Fair Lady @ Alhambra Theatre
- Yoga at the Pavilion @ Seawalk Pavilion
- BINGO @ Tom and Betty’s Restaurant
- Open Mic @ Whiskey Jax Kitchen & Cocktails
- Bar Room Dancing @ Arnolds Lounge
- Fly By Night @ Limelight Theater
- Karaoke @ Callahan’s Irish Bistro
- Trivia @ Bottleneck Brewing
- Trivia @ Moon Dog Pie House
- Trivia @ The Back 40 Urban Fresh
- Trivia @ Players Grille
- Trivia @ Green Room Brewing
May 21, 2025 – Wednesday
- TRIVIA FUN @ Culhane’s Irish Pub (Atlantic Beach)
- Trivia Fun @ Culhane’s Irish Pub (Southside)
- Free Museum Nights @ MOCA
- Jazz in the Park with Joe Watts @ JWJ Park
- NUSA 50th Golden Anniversary & Annual Conference @ Prime F. Osborn III Convention Center
- MAX DIAZ, BRAYTON, NEWLY OPPOSED @ Underbelly
- Jacksonville Jumbo Shrimp vs. Memphis Redbirds @ VyStar Ballpark
- Improv Night @ Colonial Oak Music Park
- Wednesday Live @ Gusto A Taste Of Rome
- BINGO @ Tom and Betty’s Restaurant
- Karaoke Night @ Whiskey Jax Kitchen & Cocktails
- Cookin in the Kitchen @ Prohibition Kitchen
- Live Music by Chubby G @ The Tides Oyster Co. & Grill
- Trivia @ Murray Bros. Caddyshack
- Trivia @ Mossfire Grill
- Trivia @ Fore Score Golf Tavern
- Trivia @ Time Out Sports Grill
May 22, 2025 – Thursday
- TRIVIA FUN @ Culhane’s Irish Pub (Atlantic Beach)
- Jacksonville Jazz Piano Competition @ Florida Theatre
- At the Ballet – Symphony in 60 @ Jacksonville Center for Performing Arts
- Electronic Thursdays Presents: Space Wizard @ Myth Nightclub
- NUSA 50th Golden Anniversary & Annual Conference @ Prime F. Osborn III Convention Center
- Jacksonville Jumbo Shrimp vs. Memphis Redbirds @ VyStar Ballpark
- My Fair Lady @ Alhambra Theatre
- The Boogie Freaks @ Gusto A Taste Of Rome
- Yamaneika Saunders @ The Comedy Zone
- Trivia @ Tom and Betty’s Restaurant
- Trivia Nation Thursday @ Whiskey Jax Kitchen & Cocktails
- Country Night w/ the Cam Wheaton Band @ Colonial Oak Music Park
- Karaoke w/ Gregg “Mr. Natural” Chirico @ Arnolds Lounge
- Fly By Night @ Limelight Theater
- Trivia @ Bottlenose Brewing
- Trivia @ Falafel X Bar
- Trivia @ Green Room Brewery
May 23, 2025 – Friday
- Live Music @ Culhane’s Irish Pub (Atlantic Beach)
- Karaoke Party with DJ Guru @ Culhane’s Irish Pub (Southside)
- Music by Spektra! @ Jerry’s Sports Grille
- One Stoplight Town @ Artist Connection Theatre
- PEELANDER-Z, and guests @ Jack Rabbits Live
- At the Ballet – Matinee @ Jacksonville Center for Performing Arts
- NUSA 50th Golden Anniversary & Annual Conference @ Prime F. Osborn III Convention Center
- Jacksonville Jumbo Shrimp vs. Memphis Redbirds @ VyStar Ballpark
- My Fair Lady @ Alhambra Theatre
- Spencer Thomas @ Blue Jay Listening Room
- The Main Event @ First Coast Comedy
- The Blue Show: Adults-Only Improv Comedy @ First Coast Comedy
- Bold City Classics Band @ Gusto A Taste Of Rome
- Yamaneika Saunders @ The Comedy Zone
- High N Tight @ Tom and Betty’s Restaurant
- The Good Souls @ Pusser’s Bar and Grill
- Live Music @ Whiskey Jax Kitchen & Cocktails
- Boogie Freaks @ Arnolds Lounge
- Fly By Night @ Limelight Theater
- The Collective @ Prohibition Kitchen
- Mandalla @ Prohibition Kitchen
- Trivia @ Time Out Sports Grill
- Trivia @ MVP’s Sports Grille
- Trivia @ Legacy Ale Works
May 24, 2025 – Saturday
- Karaoke Party with DJ Guru @ Culhane’s Irish Pub (Southside)
- One Stoplight Town @ Artist Connection Theatre
- VyStar Free Saturdays @ MOCA
- HERD THE CAT, and guests @ Jack Rabbits Live
- Broadway Blockbusters @ Ritz Theatre and Museum
- Jacksonville Jumbo Shrimp vs. Memphis Redbirds @ VyStar Ballpark
- My Fair Lady @ Alhambra Theatre
- The Main Event @ First Coast Comedy
- The Blue Show: Adults-Only Improv Comedy @ First Coast Comedy
- The Midnight Hour @ First Coast Comedy
- Last2leave Band @ Gusto A Taste Of Rome
- Yamaneika Saunders @ The Comedy Zone
- Curtis Willis @ Tom and Betty’s Restaurant
- Chilly Rhino @ Pusser’s Bar and Grill
- Live Music @ Whiskey Jax Kitchen & Cocktails
- Fly By Night @ Limelight Theater
- Fat Cactus @ Prohibition Kitchen
- Live Wildly presents: JJ Grey’s Blackwater Sol Revue @ St. Augustine Amphitheater
- Live Music by Vinny Jacobs! @ The Tides Oyster Co. & Grill
May 25, 2025 – Sunday
- One Stoplight Town @ Artist Connection Theatre
- Frankie Valli and The Four Seasons @ Florida Theatre
- DARUDE Live @ Myth Nightclub
- Jacksonville Jumbo Shrimp vs. Memphis Redbirds @ VyStar Ballpark
- My Fair Lady @ Alhambra Theatre
- Better Than Monday @ Pusser’s Bar and Grill
- Blistur @ Arnolds Lounge
- Fly By Night @ Limelight Theater
- Kyra Livingston @ Prohibition Kitchen
- 418 Band @ Prohibition Kitchen
- Live Wildly presents: JJ Grey’s Blackwater Sol Revue @ St. Augustine Amphitheater
May 26, 2025 – Monday
- Open Mic @ Culhane’s Irish Pub (Atlantic Beach)
- Family Feud with DJ Chris @ Disco Witch Brewing
- Jam Session with BUD @ Whitey’s Fish Camp
- Trivia @ Hibernia Pub
- Trivia @ American Legion Post
- Trivia @ The Brew Shed
- Karaoke @ The Palace Saloon
- Sam McDonald @ PJD’s
May 27, 2025 – Tuesday
- Trivia Fun @ Culhane’s Irish Pub (Southside)
- Not your Mother’s Book Club – Sky Daddy @ Happy Medium Books Cafe
- My Fair Lady @ Alhambra Theatre
- BINGO @ Tom and Betty’s Restaurant
- Open Mic @ Whiskey Jax Kitchen & Cocktails
- Bar Room Dancing @ Arnolds Lounge
- Karaoke @ Callahan’s Irish Bistro
- Trivia @ Bottleneck Brewing
- Trivia @ Moon Dog Pie House
- Trivia @ The Back 40 Urban Fresh
- Trivia @ Players Grille
- Trivia @ Green Room Brewing
- Trivia @ Time Out Sports Grill
May 28, 2025 – Wednesday
- TRIVIA FUN @ Culhane’s Irish Pub (Atlantic Beach)
- Trivia Fun @ Culhane’s Irish Pub (Southside)
- Jazz in the Park with Joe Watts @ JWJ Park
- HAYWIRE @ Underbelly
- My Fair Lady @ Alhambra Theatre
- Improv Night @ Colonial Oak Music Park
- Wednesday Live @ Gusto A Taste Of Rome
- BINGO @ Tom and Betty’s Restaurant
- Karaoke Night @ Whiskey Jax Kitchen & Cocktails
- Cookin in the Kitchen @ Prohibition Kitchen
- Live Music by Chubby G @ The Tides Oyster Co. & Grill
- Trivia @ Murray Bros. Caddyshack
- Trivia @ Mossfire Grill
- Trivia @ Fore Score Golf Tavern
May 29, 2025 – Thursday
- TRIVIA FUN @ Culhane’s Irish Pub (Atlantic Beach)
- Untold Stories @ Florida Theatre
- Tyler Childers: On The Road @ VyStar Veterans Memorial Arena
- My Fair Lady @ Alhambra Theatre
- Sidewalk 65 Band @ Gusto A Taste Of Rome
- Jackie Fabulous @ The Comedy Zone
- Trivia @ Tom and Betty’s Restaurant
- Trivia Nation Thursday @ Whiskey Jax Kitchen & Cocktails
- Country Night w/ the Cam Wheaton Band @ Colonial Oak Music Park
- Karaoke w/ Gregg “Mr. Natural” Chirico @ Arnolds Lounge
- Rhinoceros @ Limelight Theater
- House Cats @ Prohibition Kitchen
- Rick Springfield: I Want My 80’s Tour @ St. Augustine Amphitheater
- Trivia @ Bottlenose Brewing
- Trivia @ Falafel X Bar
- Trivia @ Green Room Brewery
May 30, 2025 – Friday
- Live Music @ Culhane’s Irish Pub (Atlantic Beach)
- Karaoke Party with DJ Guru @ Culhane’s Irish Pub (Southside)
- Music by Wes Cobb! @ Jerry’s Sports Grille
- Hopelessly Devoted: Olivia Newton-John & Ladies of the 80s @ Jacksonville Center for Performing Arts
- Last Friday Vendor Market @ Kava and Company (San Marco)
- Electro Lounge Night Out at the Planetarium @ MOSH
- My Fair Lady @ Alhambra Theatre
- The Main Event @ First Coast Comedy
- Jackie Fabulous @ The Comedy Zone
- Double Down @ Tom and Betty’s Restaurant
- Auggy Style @ Arnolds Lounge
- Rhinoceros @ Limelight Theater
- Good Pluck Trio @ Prohibition Kitchen
- Chillula @ Prohibition Kitchen
- Sam Barber – Restless Mind Tour @ St. Augustine Amphitheater
- Live Music by Rob Peck! @ The Tides Oyster Co. & Grill
- Trivia @ Time Out Sports Grill
- Trivia @ MVP’s Sports Grille
- Trivia @ Legacy Ale Works
May 31, 2025 – Saturday
- Karaoke Party with DJ Guru @ Culhane’s Irish Pub (Southside)
- VyStar Free Saturdays @ MOCA
- Kodak Black – Young Cash & Friends Birthday Bash @ Daily’s Place Amphitheater
- KISST LIVE in Concert @ Eclipse Nightclub & Bar
- Hopelessly Devoted: Olivia Newton-John & Ladies of the 80s @ Jacksonville Center for Performing Arts
- Retro Party feat. JOSH LAWRENCE @ Myth Nightclub
- BKB 41 Brawl in Duval II @ Prime F. Osborn III Convention Center
- EMERY ‘THE QUESTION’ TWENTY YEAR TOUR w/ ‘68 & FLAKE @ Underbelly
- My Fair Lady @ Alhambra Theatre
- The Main Event @ First Coast Comedy
- The Blue Show: Adults-Only Improv Comedy @ First Coast Comedy
- Marshville Grass Music @ Disco Witch Brewing
- Jackie Fabulous @ The Comedy Zone
- The Remains @ Arnolds Lounge
- Rhinoceros @ Limelight Theater
- Trae Pierce & the T Stones @ Prohibition Kitchen
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