2025 Key West Calendar of Events
SEPTEMBER 2025
August 29-September 1, 2025
2ND ANNUAL JUST A FEW FRIENDS-FAVORITE SON CELEBRATION
September 3-7
WOMEN FEST
September 28, 2025
PUDDLES PITY PARTY @ KEY WEST THEATER
OCTOBER 2025
October 9
TOM SANDOVAL & THE MOST EXTRAS @ KEY WEST THEATER
October 10
HILARIOUSLY INAPPROPRIATE DRAG QUEEN BINGO – A COMEDY SHOW WITH BALLS @ KEY WEST THEATER
October 10
MEGHAN BARTER: HUMAN JUKEBOX RELEASE CONCERT + LISTENING PARTY @ KEY WEST THEATER
October 11
PETER ANTONIOU “PSYCHIC COMEDIAN” @ KEY WEST THEATER
October 17-19
BAHAMA VILLAGE GOOMBAY FESTIVAL.
October 17-26
FANTASY FEST
October 17
FANTASY FEST – 2025 Royal Coronation Ball: The Vrowning of the King & Queen of Fantasy Fest
October 17-23
LOST. LUST. DUST: A NEVERLAND CABARET @ KEY WEST THEATER
October 19
ZOMBIE BIKE RIDE
October 23
FANTASY FEST-KEY WEST HEADDRESS BALL
October 24
MACY GRAY – ON HOW LIFE IS 25TH ANNIVERSARY TOUR @ KEY WEST THEATER
October 24
MASQUERADE MARCH & OurKeyWest LOCALS PARADE PARTY
October 30
THE MARGARITA BROTHERS @ KEY WEST THEATER
October 31
WILL KIMBROUGH @ KEY WEST THEATER
October 31
BUFFETT THROUGH THE YEARS – TRIBUTE @ KEY WEST THEATER
NOVEMBER 2025
November 1, 2025
DEAD-ZEP
November 2-9
WORLD OFFSHORE POWERBOAT CHAMPIONSHIP
November 7
THOMAS DOLBY “THE ICON OF THE 80’S” @ KEY WEST THEATER
November 8
WHEELAND BROTHERS @ KEY WEST THEATER
November (date TBA)
KEY WEST FILM FESTIVAL 2025
November 12
ELTON DAN @ KEY WEST THEATER
November 15
THE GARCIA PROJECT: Performing full, classic Jerry Garcia set lists from 1976-1995
November 16
GOLDEN GIRLS: THE TRIBUTE SHOW – A DRAG PARODY @ KEY WEST THEATER
November 16
Work-in-Progress Preview Screening: The Life & Art of Eric Anfinson @ The Studios of Key West
November 22
CRYSTAL GAYLE @ KEY WEST THEATER
November 24
THE CAROLE KING & JAMES TAYLOR STORY ft PHOEBE KATIS & DAN CLEWS @ KEY WEST THEATER
November 26
TONY BALTIMORE- DINNER & A SHOW ft TIM CONROY & RANDY STINDT @ KEY WEST THEATER
November 29
THE BROKEN HEARTS @ KEY WEST THEATER
December
December 4, 5, & 6
MAC MCANALLY @ KEY WEST THEATER
December 6
KEY WEST CHRISTMAS PARADE
December 10
FEMMES OF ROCK @ KEY WEST THEATER
December 11
SCOTT KIRBY – 35 YEARS OF SONGS & STORIES @ KEY WEST THEATER
December 11
ANTHONY RODIA: LAUGH TILL IT HURTS TOUR @ KEY WEST THEATER
December 13
KEY WEST LIGHTED BOAT PARADE
December 16
AN EVENING AGLOW: A CANDLELIGHT CHRISTMAS WITH MARJORY LEE @ KEY WEST THEATER
December 26
SCOTT KIRBY – 35 YEARS OF SONGS & STORIES w GABRIEL DONOHUE @ KEY WEST THEATER
December 31
NEW YEAR’S EVE CELEBRATIONS
Schooner Wharf “Rigging” in the New Year!
Sloppy Joe’s Conch Shell Drop
Bourbon Street Pub Shoe Drop
2026 Key West Calendar of Events
January 2 & 3
SCOTT KIRBY – 35 YEARS OF SONGS & STORIES w NOAH ROBERTSON @ KEY WEST THEATER
January 8-11
KEY WEST LITERARY SEMINAR
January 8
BEN HARRISON @ KEY WEST THEATER
January 11
DAVID NIHILL: TAKING TANGENTS TOUR @ KEY WEST THEATER
January 13th
LOS LOBOS DISCONNECTED @ KEY WEST THEATER
January 14th
THE EXPANDING MAN: AN ORIGINAL TRIBUTE TO STEELY DAN @ KEY WEST THEATER
January 15th
SCOTT KIRBY- 35 YEARS OF SONGS & STORIES W/ CAFFEINE CARL @ KEY WEST THEATER
January 15th
ASLEEP AT THE WHEEL @ KEY WEST THEATER
January 16th
KASH’D OUT @ KEY WEST THEATER
January 16th
THE CORAL REEFER BAND @ COFFEE BUTLER AMPHITHEATER
January 17th
THE BRIT PACK @ THE KEY WEST THEATER
January 21st
RUMORS ATL: A FLEETWOOD MAC TRIBUTE @ KEY WEST THEATER
January 21
BEN HARRISON @ KEY WEST THEATER
January 26
THE PHIL COLLINS EXPERIENCE @ KEY WEST THEATER
January 27-31
MILE 0 FEST
FEBRUARY 2026
February 4
The Massacoustics @ The Key West Theater
February 12-13
Scott Kirby- 35 Years of Songs & Stories w/ Mike Michaels @ The Key West Theater
February 14
A Tribute to The Songs of Pat Dailey w. Ray Fogg and Reese Dailey @ The Key West Theater
February 15
Gabriel Rutledge: Don’t Read the Comments Tour @ The Key West Theater
February 17
Ben Harrison @ Key West Theater
February 18
Yachtley Crew @ Key West Theater
February 21-22
Key West Art & Crafts Festival
February 21
The Linda Ronstadt Experience @ Key West Theater
February 25 & 26
Scott Kirby- 35 Years of Songs & Stories w/ Dave Edmisten @ Key West Theater
February 25
DMTB: The Dave Matthews Tribute Band @ Key West Theater
MARCH 2026
March 3
Changes In Latitude @ Key West Theater
March 5
Ben Harrison @ Key West Theater
March 7
Key West Conch Blowing Contest @ The Oldest House
March 14
48th ANNUAL ST. PATRICK’S DAY BAR STROLL
March 18
CONCH REVIVAL PICNIC
March 21
The Reverend Peyton’s Big Damn Band @ Key West Theater
March 22
Tommy Emmanuel CGP – Living In The Light Tour @ Key West Theater
March TBA
TASTE OF KEY WEST
March 25
Ben Harrison @ Key West Theater
March 27
7 Bridges: The Ultimate Eagles Experience @ Key West Theater
March TBA
KEY WEST SAILFISH TOURNAMENT
APRIL 2026
April 17-26
44RD ANNUAL CONCH REPUBLIC DAYS
April 29-May 3
KEY WEST SONGWRITERS FESTIVAL
—Archived 2025 Key West Calendar of Events—
JANUARY 2025
Jan 09-12
KEY WEST LITERARY SEMINAR
Jan 21-26
KEY WEST FOOD & WINE FESTIVAL
Jan 21-25
MILE 0 FEST
Jan 22
MELISSA ETHERIDGE: 2025 TOUR
January 28-February 1
KEY WEST FOOD & WINE FESTIVAL
Jan 31
CHICAGO – LIVE IN CONCERT @ COFFEE BUTLER AMPHITHEATER
Jan 31
HEMINGWAY IN A FUNNY WAY
FEBRUARY 2025
February 1
The Brit Pack: The Ultimate British Music Experience
February 4
STUDIOS OF KEY WEST: WILL KIMBROUGH IN CONCERT
February 05
The Reverend Peyton’s Big Damn Band
February 8
GIPSY KINGS @ Coffee Butler Amphitheater
February 9
THE MAN IN BLACK: A TRIBUTE TO JOHNNY CASH
February 11
Diana’s Stop In The Name of Love Tour with Motown & More Motown
February 12 & 13
Scott Kirby w. Ashley Bathgate
February 14
WILLIE NELSON & FAMILY @ Coffee Butler Amphitheater
February 14
Island Love Stories: Valentine’s Day Concert @ Key West Theater
February 16
DEBBIE GIBSON @ Key West Theater
February 20
NICK SWARDSON @ Key West Theater
February 21
LET’S DISCO – KEY WEST ART & HISTORICAL SOCIETY ANNUAL FUNDRAISER
February 22
KELLER WILLIAMS @ Key West Theater
February 22-23
KEY WEST ART & CRAFT FESTIVAL
February 26
THE PHIL COLLINS EXPERIENCE @ Key West Theater
February 28
THE BEACH BOYS @ Coffee Butler Amphitheater
MARCH 2025
March 1
8th Annual Manny Madruga Domino Tournament
March 2
KEVIN NEALON @ KEY WEST THEATER
March 6
KEY WEST LITERARY SEMINAR: ELIZABETH BISHOP HOUSE & GARDEN OPENING
March 8
CONCH BLOWING CONTEST
March 8
BRETT YOUNG @ Coffee Butler Amphitheater
March 11
CONCH REVIVAL PICNIC
March 15
47th ANNUAL ST. PATRICK’S DAY BAR STROLL
March 18-19
STUDIO OF KEY WEST: BETH CHAPMAN IN CONCERT
March 20
WALK ON WHITE
March 24
TASTE OF KEY WEST
March 26
TENNESSEE WILLIAMS BIRTHDAY PARTY
March 27-29
KEY WEST SAILFISH TOURNAMENT
March 28 & 29
KEITH SYKES @ The Key West Theater
March 29-30
NAS KEY WEST: SOUTHERNMOST AIR SHOW SPECTACULAR
APRIL 2025
April 3-24
STUDIOS OF KEY WEST: A FIFTY-YEAR RETROSPECTIVE WITH WORKS BY DAVID WEGMAN
April 18-25
43RD ANNUAL CONCH REPUBLIC DAYS
April 30-May 4
KEY WEST SONGWRITERS FESTIVAL
MAY 2025
May 1-29th
STUDIOS OF KEY WEST: ISAAC VALDES-THE WAY IT WAS
May 22nd
TRUMAN WATERFRONT FARMERS MARKET – EVERY THURSDAY
May 25th
34TH ANNUAL SCHOONER WHARF MINIMAL REGATTA
May 29th
TRUMAN WATERFRONT FARMERS MARKET – EVERY THURSDAY
June 2025
June 1-20th
SUMMER SOLSTICE CELEBRATION AT MALLORY SQUARE – EVERY DAY
June 5-July 31
STUDIOS OF KEY WEST: MANGO MADNESS ANNUAL SUMMER MEMBERS SHOW
June 7th
REEF RELIEF: INTERNATIONAL OCEAN FILM FESTIVAL
June 19th
WALK ON WHITE – 3RD THURSDAY EVERY MONTH
June 22-29th
KEY WEST PRIDE WEEK
June 28
49th ANNUAL SWIM AROUND THE ISLAND
June 29
JEFF DYE @ THE KEY WEST THEATER
JULY 2025
4th of JULY FIREWORK CRUISES – Lots of Options to Choose From
July 3-7
KEY WEST KEY LIME FESTIVAL
July 5, 2025
FIGHTING FOR LAUGHS – A NIGHT OF COMEDY 4 AHERO
July 23-27
HEMINGWAY DAYS & 43rd LOOK-ALIKE CONTEST
July 23-26
KEY WEST MARLIN TOURNAMENT
July 30-31
LOBSTER MINI SEASON
AUGUST 2025
August 7-10
28th ANNUAL LOBSTERFEST
August 13-17
TROPICAL HEAT
August 11-17
KEY WEST RUM FESTIVAL
August 29-September 1, 2025
2ND ANNUAL JUST A FEW FRIENDS-FAVORITE SON CELEBRATION
August 30, 2025
PARROTS & MARGARITAS 5K
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