2026 Key West Calendar of Events
Looking for what’s happening in Key West? Here’s your curated guide to concerts, festivals, cultural happenings, races, and local favorites — updated monthly.
Last updated: April 2026
Planning your trip around a festival, concert, or special event? Book early—Key West’s busiest weekends fill fast.
Jump to: April · May · June · July · August · September · October · November · December
44th Annual Conch Republic Days
A signature Key West celebration filled with island spirit, quirky traditions, and events across town.
Key West Songwriters Festival
One of the largest songwriter festivals in the world, featuring live performances across iconic Key West venues. Plan ahead—this is one of Key West’s busiest weekends.
APRIL 2026 – KEY WEST EVENTS
Festival season peaks with Conch Republic Days and spring concerts.
April 2–4
Spanish Fly Shark Tournament
April 2
Squirrel Nut Zippers @ Key West Theater
April 3 & 4
Keith Sykes @ Key West Theater
April 7
Crystal Gayle @ Key West Theater
April 11
7 Mile Bridge Run
April 12
Good Trees River Band @ Key West Theater
April 12
Donovan Frankenreiter w/ Iris in the Shade @ Key West Theater
April 16
Imagine a Dragon @ Key West Theater
April 17–26
44th Annual Conch Republic Days
April 18
MetalrItaville @ Key West Theater
April 19
Cow Key Bridge Run (0K)
April 22
Earth Day Jam with That Hippie Collective @ Key West Theater
April 23
Foreigner 4 with Special Appearance by Lou Gramm @ Coffee Butler Amphitheater
April 24
Follow the Rabbit @ Key West Theater (6 & 9 PM)
April 25
Mote’s Ocean Fest @ Truman Waterfront Park
April 25
5th Annual Cuban Sandwich Throwdown @ Green Parrot (Noon)
April 25 & 26
Graham Nash @ Key West Theater
April 26
The Ocean Hates You! @ Comedy Key West
April 27
Where’s Dave Band @ Key West Theater
April 29
Nick Norman w/ Adam Wood @ Key West Theater
April 29–May 3
Key West Songwriters Festival
Planning ahead? Explore upcoming Key West events by month.
MAY 2026 – KEY WEST EVENTS
Songwriters, live music, and laid-back island events.
Key West Songwriters Festival
One of the largest songwriter festivals in the world, featuring live performances across iconic Key West venues.
May 1–3
You’re a Good Man, Charlie Brown @ Red Barn Theatre
May 2
Talk Derby to Me – Kentucky Derby Event @ The Gardens Hotel
May 7 & 8
Playwrights Festival @ Williams Hall
May 9
George Thorogood & The Destroyers w/ The Marshall Tucker Band @ Key West Theater
May 10
10,000 Maniacs @ Key West Theater
May 15
Tri Not to Rock @ Key West Theater
JUNE 2026 – KEY WEST EVENTS
Pride Week and summer events kick off across Key West.
Key West Pride Week
A vibrant, weeklong celebration of love, community, and island spirit with events across Key West.
June 4
Mango Madness Annual Art Exhibition Opening @ The Studios of Key West
June 5
Bertha: Grateful Drag @ Key West Theater
June 9
Steve Earle @ Key West Theater
June 13
Swim Around Key West
JULY 2026 – KEY WEST EVENTS
Key Lime Festival
A zesty, weeklong celebration of Key West’s most iconic dessert with tastings, competitions, and culinary events.
Hemingway Days
A beloved Key West tradition celebrating Ernest Hemingway with literary events, street festivities, and the famous look-alike contest. Plan ahead—this is one of Key West’s busiest weekends.
July 4
4th of July Spectacular
July 22–25
Key West Marlin Tournament
July 29–30
Lobster Mini Season
AUGUST 2026 – KEY WEST EVENTS
Rum Fest
A spirited week of tastings, events, and island celebrations honoring Key West’s rich rum culture.
August 5–9
Key West Lobsterfest
August 14
Rum Fest: Cliff Cody & Sharese @ Key West Theater
August 15
Jesse Rice @ Key West Theater
SEPTEMBER 2025 – KEY WEST EVENTS
Just a Few Friends – Favorite Son Celebration
A tribute to Jimmy Buffett with live music, gatherings, and island-wide celebrations. A popular time to visit—book early for the best availability.
September 3–7
Womenfest
September 4
Through the Lens: Early Buffett Concert Photography Exhibit @ The Pier House
September 28, 2025
Puddles Pity Party @ Key West Theater
OCTOBER 2026 – KEY WEST EVENTS
Goombay Festival
A lively celebration of Bahamian culture in Key West with music, food, and dancing in the streets of Bahama Village.
Fantasy Fest & 2026 Parade
The grand finale of Fantasy Fest featuring elaborate floats, costumes, and one of Key West’s most iconic nights. Plan ahead—this is one of Key West’s busiest weekends.
October 18
Zombie Bike Ride
October 23
Local’s Masquerade March
October 25
Children’s Day
October 27
Garrison Keillor & Erica Rhodes @ Key West Theater
October 30
Buffett Through the Years @ Key West Theater
October 28–November 1
Gathering of the Order of the Sleepless Knights
NOVEMBER 2026 – KEY WEST EVENTS
Race World Offshore World Championship
High-speed offshore racing returns to Key West with a full week of competition, festivities, and waterfront excitement.
Key West Film Festival
A celebrated annual festival showcasing independent films, premieres, and industry talent in venues across Key West.
November 7
The Ocean Blue @ Key West Theater
November 8
Bruce Cockburn & Livingston Taylor @ Key West Theater
November 19
Marty Stuart & His Fabulous Superlatives @ Key West Theater
November 20 & 21
Dusty Slay @ Key West Theater
November 22
Buena Vista Social Club @ Key West Theater
DECEMBER 2026 – KEY WEST EVENTS
New Year’s Eve Celebrations
Ring in the New Year Key West-style with iconic drops including the Schooner Wharf “Rigging,” Sloppy Joe’s Conch Shell, and the Bourbon Street Pub Shoe. Plan ahead—this is one of Key West’s busiest weekends.
All Month Long
Key West Harbor Walk of Lights
December (TBA)
Nutcracker Ballet
December 5
Key West Holiday Parade
December 13
Key West Lighted Boat Parade
Past 2026 Events
Browse earlier 2026 events by month.
MARCH 2026 – KEY WEST EVENTS
March 2
Lost Kitchen Supper Club – Cuban Style Pig Roast
March 3 & 4
Changes in Latitude @ Key West Theater
March 5
Ben Harrison @ Key West Theater
March 5
The Man in Black: Tribute to Johnny Cash @ Key West Theater
March 6
Nick Norman w/ Joal Rush @ Key West Theater
March 6, 7 & 8
Annual Key West Orchid Society Festival @ West Martello Gardens
March 7
Brian Imbus: Mentalist and Hypnotist @ Key West Theater
March 7
Key West Conch Blowing Contest @ The Oldest House
March 8
Open Studio Tours for the Stockyard Studios
March 11
Scott Kirby – 35 Years of Songs & Stories w/ Davin James @ Key West Theater
March 13 & 14
Jammy Buffet w/ Special Guest Peter Mayer
March 13
John Frinzi & Aaron Scherz @ Key West Theater
March 14
Martin Sexton @ Key West Theater
March 14
Kim Gordon’s Black & Red Masquerade Ball @ Key West Theater
March 13 & 14
Old Island Restoration Home Tour
March 14-17
St. Patrick’s Day Events
March 14
48th Annual St. Patrick’s Day Bar Stroll
March 15
Golden Girls: The Tribute Show – A Drag Parody @ Key West Theater
March 15
Hilariously Inappropriate Drag Queen Bingo • A Comedy Show With Balls @ Key West Theater
March 17
St. Patrick’s Day Events
March 17
Echos of Eric Presented by Suzanne Moore @ Key West Theater
March 18
Nick Brownell, Jeff Harris and Ray Fogg – Hey, We Write Nice Songs Too! @ Key West Theater
March 18
Conch Revival Picnic
March 19
Larry Joe Taylor & Guest @ Key West Theater
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 23
Taste of Key West
March 25
Ben Harrison @ Key West Theater
March 25
Tennessee Williams Birthday Party
March 25
Bumpin Uglies w/ Joey Harkum @ Key West Theater
March 26-28
Key West Sailfish Tournament
March 27
Nick Norman @ Key West Theater
March 27
7 Bridges: The Ultimate Eagles Experience @ Key West Theater
March 28
Follow the Rabbit @ Key West Theater
March 28
The 77 Experience (A Journey Thru Rock and Roll History Plus Much More) @ Key West Theater
March 29
BoDeans: 40 Years of Love & Hope & Sex & Dreams… and Good Things @ Key West Theater
March 29
The Beach Boys @ Key West Theater
March 31-April 25
A Rock Sails By @ Red Barn Theater
FEBRUARY 2026 – KEY WEST EVENTS
February 1
Nick Norman, Shane Williams & Warren Bazemore @ Key West Theater
February 4 & 5
The Massacoustics @ Key West Theater
February 5
Ben Harrison @ Key West Theater
February 6 & 7
Mary Gauthier @ Key West Theater
February 8
Key West Artisan Market @ Higgs Beach
February 8
2026 Annual Southernmost Conch Republic Polar Plunge
February 8
Super Bowl Party @ The Empourium
February 10 & 11
Brian Patafies – Funny as Puck Tour @ Key West Theater
February 12 & 13
Scott Kirby – 35 Years of Songs & Stories w/ Mike Michaels @ Key West Theater
February 13
Benmont Tench @ Key West Theater
February 13 & 14
Old Island Restoration – January Home Tours
February 14
A Tribute to the Songs of Pat Dailey w/ Ray Fogg and Reese Dailey @ Key West Theater
February 14 & 15
Florida Keys Seafood Festival
February 15
Gabriel Rutledge: Don’t Read the Comments Tour @ Key West Theater
February 17
Ben Harrison @ Key West Theater
February 18
Yachtley Crew @ Key West Theater
February 19
The Old Fashion Rocking Original Music Show @ Key West Theater
February 20
Carson Lowe Single Release @ Key West Theater
February 21 & 22
Key West Art & Crafts Festival
February 21
The Linda Ronstadt Experience @ Key West Theater
February 22
Big Bad Voodoo Daddy @ Key West Theater
February 24–March 21
And the World Goes ’Round @ Red Barn Theatre
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
February 27
Follow the Rabbit @ Key West Theater
February 27
Colin Quinn @ Key West Theater
JANUARY 2026 – KEY WEST 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 10
GIVEN TO FLY: A TRIBUTE TO PEARL JAM @ KEY WEST THEATER
January 11
DAVID NIHILL: TAKING TANGENTS TOUR @ KEY WEST THEATER
January 12
THE 5TH ANNUAL IGGIE’S: KEY WEST MUISC AWARDS @ KEY WEST THEATER
January 13
LOS LOBOS DISCONNECTED @ KEY WEST THEATER
January 14
THE EXPANDING MAN: AN ORIGINAL TRIBUTE TO STEELY DAN @ KEY WEST THEATER
January 15
SCOTT KIRBY- 35 YEARS OF SONGS & STORIES W/ CAFFEINE CARL @ KEY WEST THEATER
January 15
ASLEEP AT THE WHEEL @ KEY WEST THEATER
January 16
KASH’D OUT @ KEY WEST THEATER
January 16
THE CORAL REEFER BAND @ COFFEE BUTLER AMPHITHEATER
January 17
THE BRIT PACK @ THE KEY WEST THEATER
January 17
PETER MAYER & FRIENDS @ THE KEY WEST THEATER
January 17-18
KEY WEST HALF MARATHON & 5K
January 19-23
SOUTHERNMOST REGATTA
January 20
AT THE WEDDING @ RED BARN THEATER
January 20-26
KELLY MCGILLIS CLASSIC
January 21
RUMORS ATL: A FLEETWOOD MAC TRIBUTE @ KEY WEST THEATER
January 21
BEN HARRISON @ KEY WEST THEATER
January 23
YOUNG DUBLINERS @ KEY WEST THEATER
January 23 & 24
Old Island Restoration – January Home Tours
January 25
Peyton Porter @ Key West Theater
January 26
Andrew Duhon @ Key West Theater
January 26
THE PHIL COLLINS EXPERIENCE @ KEY WEST THEATER
January 27-31
MILE 0 FEST
January 28-February 1
KEY WEST FOOD & WINE FESTIVAL
January 28
ALICE HOWE & FREEBO @ KEY WEST THEATER
January 29
SCOTT KIRBY @ KEY WEST THEATER
January 30
THE JANZEN BOYS @ KEY WEST THEATER
January 31
FOLLOW THE RABBITT @ KEY WEST THEATER
2025 Archived Events
Browse past Key West events from 2025.
JANUARY 2025 – KEY WEST EVENTS
January 9–12
Key West Literary Seminar
January 21–26
Key West Food & Wine Festival
January 21–25
Mile 0 Fest
January 22
Melissa Etheridge: 2025 Tour
January 28–February 1
Key West Food & Wine Festival
January 31
Chicago – Live in Concert @ Coffee Butler Amphitheater
January 31
Hemingway in a Funny Way
FEBRUARY 2025 – KEY WEST EVENTS
February 1
The Brit Pack: The Ultimate British Music Experience
February 4
Studios of Key West: Will Kimbrough in Concert
February 5
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 – KEY WEST EVENTS
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
Studios 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 – KEY WEST EVENTS
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 – KEY WEST EVENTS
May 1–29
Studios of Key West: Isaac Valdes – The Way It Was
May 22
Truman Waterfront Farmers Market – Every Thursday
May 25
34th Annual Schooner Wharf Minimal Regatta
May 29
Truman Waterfront Farmers Market – Every Thursday
JUNE 2025 – KEY WEST EVENTS
June 1–20
Summer Solstice Celebration at Mallory Square – Every Day
June 5–July 31
Studios of Key West: Mango Madness Annual Summer Members Show
June 7
Reef Relief: International Ocean Film Festival
June 19
Walk on White – 3rd Thursday Every Month
June 22–29
Key West Pride Week
June 28
49th Annual Swim Around the Island
June 29
Jeff Dye @ The Key West Theater
JULY 2025 – KEY WEST EVENTS
Holiday Weekend
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 – KEY WEST EVENTS
August 7–10
28th Annual Lobsterfest
August 11–17
Key West Rum Festival
August 13–17
Tropical Heat
August 29–September 1, 2025
2nd Annual Just a Few Friends – Favorite Son Celebration
August 30, 2025
Parrots & Margaritas 5K
SEPTEMBER 2025 – KEY WEST EVENTS
August 29–September 1, 2025
2nd Annual Just a Few Friends – Favorite Son Celebration
September 3–7
Women Fest
September 4
Through the Lens: Early Buffett Concert Photography Exhibit @ The Pier House
September 28, 2025
Puddles Pity Party @ Key West Theater
OCTOBER 2025 – KEY WEST EVENTS
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 – Canceled
October 10
Meghan Barter: Human Jukebox Release Concert + Listening Party @ Key West Theater
October 11
Peter Antoniou “Psychic Comedian” @ Key West Theater
October 15–24
Rocky Horror Picture Show @ Waterfront Playhouse
October 17–19
Bahama Village Goombay Festival
October 17–26
Fantasy Fest
October 17
Fantasy Fest – Royal Coronation Ball
October 17–23
Lost. Lust. Dust: A Neverland Cabaret @ Key West Theater
October 19
Key West Artisan Market @ Higgs Beach
October 19
Zombie Bike Ride
October 20
Fantasy Fest 5K Run/Walk
October 21
Tutu Party
October 22
Past Your Bedtime @ The Hush Hush Theater
October 22
Studio 69 Disco Party
October 23
Fantasy Fest – Key West Headdress Ball
October 24
Macy Gray @ Key West Theater
October 24
Fantasy Fest Masquerade March & OurKeyWest Watch Party 🎭
October 25
Fantasy Fest Parade
October 26
Tea Dance @ La Te Da
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 – KEY WEST EVENTS
November 1, 2025
Dead-Zep
November 2–9
World Offshore Powerboat Championship & Spectator Cruise
November 7
Thomas Dolby @ Key West Theater
November 8
Wheeland Brothers @ Key West Theater
November (Date TBA)
Key West Film Festival
November 12
Elton Dan @ Key West Theater
November 15
The Garcia Project
November 16
Golden Girls Drag Tribute @ Key West Theater
November 16
Zack Seemiller: This Show Saves Lives
November 16
Eric Anfinson Film Screening @ Studios of Key West
November 21
Songs of Pete & Wayne @ Key West Theater
November 24
Carole King & James Taylor Story @ Key West Theater
November 26
Tony Baltimore Dinner & Show @ Key West Theater
November 29
The Broken Hearts @ Key West Theater
November 29
30th Annual 5K Hog Trot
DECEMBER 2025 – KEY WEST EVENTS
All Month Long
Key West Harbor Walk of Lights
December 4
20th Annual Pet Pictures with Santa
December 4–6
Mac McAnally @ Key West Theater
December 5
Holiday Village & Bike Parade
December 6
Key West Christmas Parade
December 7
Montessori Key West 5K & Kids Run
December 9–January 3
Scrooge Macbeth @ Red Barn Theater
December 10
Femmes of Rock @ Key West Theater
December 11
Scott Kirby @ Key West Theater
December 11
Anthony Rodia @ Key West Theater
December 12 & 19
Holiday Historic Inn Tours
December 13
Gingerbread Build
December 13
Lighted Boat Parade
December 14
Menorah Lighting Ceremony
December 14
Key West Triathlon
December 16
Candlelight Christmas @ Key West Theater
December 18
Holiday Walk on White
December 21
Southernmost SantaCon
December 21
Artisan Market
December 26
Scott Kirby @ Key West Theater
December 26 & 27
Old Island Home Tours
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
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