Key West Music Events

The Fright Crawl | Key West's #1 Halloween Bar Crawl 2026 | Sat, Oct 31

TBA 31 Oct 2026

The Fright Crawl | Key West Halloween Day Bar Crawl 2026 | Sat, Oct 31

TBA 31 Oct 2026

Captain Morgan's Masquerade March

1117 Fleming St, Key West, FL 33040-6909, United States 23 Oct 2026

Fantasy Fest Street Fair & Costume Promenade

Duval St, Key West, FL 33040, United States 23 Oct 2026

The Fright Crawl | Key West Halloween Bar Crawl 2026 | Fri, Oct 30

TBA 30 Oct 2026

2026 Fantasy Fest Parade Viewing Party @ First Flight

First Flight Island Restaurant & Brewery 24 Oct 2026

"The Fat Lady Sings" Tea Dance

La Te Da 25 Oct 2026

Paparazzi Row Block Party

1129 Fleming St, Key West, FL, United States, Florida 33040 23 Oct 2026

Friday Night Fever Fantasy Fest Party at Hog's Breath *FREE EVENT*

400 Front St, Key West, FL, United States, Florida 33040 23 Oct 2026

Sloppy Joe's 47th Annual Toga Party

Sloppy Joe's Key West 22 Oct 2026

5th Annual Party Like A Rockstar Party

The Key West Empourium 21 Oct 2026

A Green Parrot Beatle Tribute

The Green Parrot 19 Oct 2026

Halloween Bar Crawl 10/31 - KEY WEST

La Concha Key West, Autograph Collection 31 Oct 2026

Halloween Eve Bar Crawl 10/30 - KEY WEST

La Concha Key West, Autograph Collection 30 Oct 2026

NINA STYLY X ELECTRONICONCH RECORDS - FASHION THROGHT SOUND

Viva Argentinian Steakhouse 23 Oct 2026

Buffett Through the Years

Key West Theater 30 Oct 2026

Sins & Sequins - An Official Fantasy Fest Event

Blue Flamingo Resort Key West 21 Oct 2026

That Arena Rock Show

0 Duval Street, Key West, FL, United States, Florida 33040 18 Oct 2026

WE LOVE DOLLY! 💖 A Dolly Parton Tribute Party

431 Front St, Key West, FL 33040-6663, United States 20 Oct 2026

Sloppy Joe's Comic Book Caper-ers Party

Sloppy Joe's Key West 19 Oct 2026

Candlelight: Coldplay vs. Imagine Dragons

Key West Theater 13 Nov 2026

Bruce Cockburn & Livingston Taylor

Key West Theater 7 Nov 2026

Irish Kevin's Annual 80's Party

211 Duval St, Key West, FL, United States, Florida 33040 22 Oct 2026

Bruce Cockburn at Key West Theater

Key West Theater 8 Nov 2026

Mamma Mia’s Margaritaville Pool Party

2001 S Roosevelt Blvd, Key West, FL 33040-5243, United States 19 Oct 2026

KEY WEST OYSTER FEST: A BENEFIT FOR THE GULF OYSTER

Half Shell Raw Bar 14 Nov 2026

A Tribute to the Songs of Pete & Wayne with Pete Jarvis, Larry Strickland, Ray Fogg & Special Guests

Key West Theatre 14 Nov 2026

The Blue Party at the Backyard Bar

The Key West Empourium 24 Oct 2026

2026 - Saturday, Oct. 31 - Jerry Diaz's Key West Sunset "Booze Cruise"!

Sebago Watersports 31 Oct 2026

Dirty Doctors Naughty Nurses Party

Southernmost Pint Brewpub - Blast Beer Company Brewery 24 Oct 2026

Candlelight: The Best of Hans Zimmer

Key West Theater 13 Nov 2026

FUNKY GRATEFUL DEAD GET DOWN PARTY (6-piece band) & 4 DJ's AFTER PARTY

Viva Argentinian Steakhouse 23 Oct 2026

Swayzees Music Icons Pool Party at Shores Pool

Southernmost Beach Resort 21 Oct 2026

Tay-Tay Tuesday - Life of a Showgirl

0 Duval Street, Key West, FL, United States, Florida 33040 20 Oct 2026

Masquerade Monday Wine Dinner Presented by Bogle Wines

A&B Lobster House 19 Oct 2026

Texas Trop Rock: Jerry Diaz, Dan Sullivan, Jonas Lorence Band

Key West Theater 31 Oct 2026

Les Greene & The Swayzees Musical Icons Pool Party Take 2 At The Marker Resort

The Marker Key West Resort 22 Oct 2026

GLAMOROUS DEAD & UNDEAD POPSTARS PARTY - at Viva's

Viva Argentinian Steakhouse 22 Oct 2026

2026 - Friday, Oct. 30 - Jerry Diaz's Key West Sunset "Booze Cruise"

Sebago Watersports 30 Oct 2026

Krewe de Krazy Life Meet and Greet and Costume Parts Exchange

Galleon Tiki Bar 18 Oct 2026

Key West Theater

Key West Theater 30 Oct 2026

Powerboat Village in the Historic Seaport!

Conch Republic Seafood Company 4 Nov 2026

Custom House Holiday Concert & Bazaar

Key West Art & Historical Society 11 Dec 2026

STUDIO 69 DISCO PARTY - at Viva's

Viva Argentinian Steakhouse 21 Oct 2026

Under the Sea Party

Dante's Pool Bar & Restaurant 19 Oct 2026

Captain Tony's Party In Plaid

Captain Tony's Saloon Key West 20 Oct 2026

Wharfstock at the Schooner Wharf Bar

Schooner Wharf Bar 21 Oct 2026

Daft After Dark / Fantasy Fest Parade Watch & After Party

1004 Duval St, Key West, FL, United States, Florida 33040 24 Oct 2026

Jazz In The Gardens!

526 Angela St 25 Oct 2026

IAN MAKSIN in KEY WEST: "SONGS of LOVE & PEACE" 2026 Concert Tour

Congregation B'nai Zion 11 Nov 2026

Candlelight: Vivaldi's Four Seasons

Key West Theater 11 Dec 2026

Candlelight: Tribute to Fleetwood Mac

Key West Theater 11 Dec 2026

Fantasy Fest Les Greene & the Swazees The Marker Key West Harbor Resort on October 22

The Marker Key West Harbor Resort 22 Oct 2026

Fantasy Fest Greatest Hits Pool Party

Winslow's Bungalows - Key West Historic Inns 20 Oct 2026

Mac McAnally in Key West

Key West Theater 18 Dec 2026

Tim Palmieri & Friends at The Green Parrot

The Green Parrot 11 Dec 2026

MANGOES FANTASY FEST PARADE PARTY

Mangoes Restaurant Key West 24 Oct 2026

Killer Prom (11/8)

Key West Theater 8 Nov 2026

The Buena Vista Orchestra

Key West Theater 22 Nov 2026

Classic Seger: Bob Seger's Greatest Hits Live (9PM)

Key West Theater 23 Jan 2027

Sunny Jim, Florida Days

Key West Theater 30 Oct 2026

Disco Fever Costume Party

Key West Gallery 22 Oct 2026

Old Crow Medicine Show in Key West

Truman Waterfront Park Amphitheater 26 Jan 2027

🎶🐣Blue Heaven🐓🎶

Blue Heaven 18 Oct 2026

Justin Angelo at Sunset Tiki

Sunset Tiki 18 Oct 2026

Studio 430 Dance Club Under The Stars!

La Concha Key West 22 Oct 2026

The Broken Hearts: A Tribute to Tom Petty & The Heartbreakers

Key West Theater 12 Dec 2026

Lolita's Look-A-Like Contest

Elevate Skye Bar & Lounge 18 Oct 2026

December Duo Holiday Concert: Irie Monte and Crispin Campbell

533 Eaton St, Key West, FL, United States, Florida 33040 12 Dec 2026

Candlelight: Christmas Classics

Key West Theater 26 Dec 2026

Bunny Pool Party - Official Fantasy Fest Event

1400 Duval St, Key West, FL, United States, Florida 33040 23 Oct 2026

An Evening Aglow: A Candlelight Christmas with Marjory Lee

Key West Theater 15 Dec 2026

Sloppy Joe's Slumber Party

Sloppy Joe's Key West 21 Oct 2026

Mac McAnally at Key West Theater

Key West Theater 18 Dec 2026

Rob Benton Concert and Pool Party at The Marker Key West Harbor Resort on November 1

The Marker Key West Harbor Resort 1 Nov 2026

Fabulous Spectrelles

Kaya Island Eats 9 Oct 2026

SING • SYNC • SLAY Karaoke Pool Party

2401 N Roosevelt Blvd, Key West, FL, United States, Florida 33040 21 Oct 2026

A Tribute to the Songs of Pat Dailey in Key West with Ray Fogg, Reese Dailey & Special Guests

Key West Theatre 13 Feb 2027

The Phil Collins Experience

Key West Theater 20 Jan 2027

The Restless Natives: Macon, Georgia's tribute to The Allman Brothers Band

Key West Theater 1 Jan 2027

Southernmost Youth Orchestra

533 Eaton St, Key West, FL, United States, Florida 33040 15 Nov 2026

Double Duran "The Ultimate Duran Duran Experience"

Key West Theater 18 Jan 2027

Third Annual Key West Woman's Club Bougie Afternoon Tea Party

319 Duval St, Key West, FL, United States, Florida 33040 16 Jan 2027

Kaitlin Butts in Key West

Truman Waterfront Park Amphitheater 26 Jan 2027

November's Walk On White

1110 White Street, Key West, FL, United States, Florida 33040 19 Nov 2026

Peter Mayer: A Stars & Promises Christmas "This Town"

Key West Theater 29 Nov 2026

Keller Williams Trio at Key West Theater

Key West Theater 2 Jan 2027

Pete Yorn at Key West Theater

Key West Theater 6 Feb 2027

3rd Annual Moose March

Key West Moose Lodge 1760 7 Mar 2027

Thanksgiving at Four Marlins

1435 Simonton St, Key West, FL, US 33040 26 Nov 2026

Mac McAnally

Key West Theater 19 Dec 2026

Will Kimbrough

Key West Theater 30 Oct 2026

Elton Dan & The Rocket Band

Key West Theater 13 Mar 2027

Kash'd Out

Key West Theater 16 Jan 2027

Scott Kirby - 36 YEARS OF SONGS AND STORIES with Gabriel Donohue

Key West Theater 26 Dec 2026

10 000 Maniacs

Key West Theater 11 Apr 2027

Sunny Jim, “The Cayman Years” in Songs and Stories

Key West Theater 29 Oct 2026

December's Walk On White

1110 White Street, Key West, FL, United States, Florida 33040 17 Dec 2026

CANN PRESENTS: YACHT ROCK REVUE - PRIMETIME

Coffee Butler Amphitheater 20 Jan 2027

January's Walk On White

1110 White Street, Key West, FL, United States, Florida 33040 21 Jan 2027