Upcoming Live Music Events

THE QUEENS OF COUNTRY: PATSY! DOLLY! LORETTA!

 319 Duval Street, Rear, 33040 7 Jan 2026
MUSIC

IAN MAKSIN in KEY WEST, FL: Songs of Love & Peace

 Williams Hall 3 Jan 2026
MUSIC

Bougie Afternoon Tea

 319 Duval St, Key West, FL 17 Jan 2026
LIVE-MUSIC

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Upcoming Festivals Events

David Nihill: Taking Tangents Tour

Key West Theater 11 Jan 2026
CONTESTS

61th Annual Key West Art & Craft Festival

 Truman Waterfront Park 21 Feb 2026
ART

"Wrong and Strong" by Juliet Dyal Gray

 Williams Hall 31 Jan 2026
FESTIVALS

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Upcoming Comedy Events

Fighting For Laughs, Too

 Kaya Island Eats 7 Feb 2026
COMEDY

Scrooge Macbeth

 319 Duval Street, Rear, 33040 1 Jan 2026
ART

Q West: Comedy Escape 2026

 Key West Theater 10 Apr 2026
COMEDY USD 450 TO 534

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Upcoming Food & Drinks Events

31st Annual Taste of Key West

 Truman Waterfront, Key West, FL, United States, Florida 33040 23 Mar 2026

GAMEDAY! College Football at Mary Ellen's!

 420 Appelrouth Lane, Key West, FL, United States, Florida 33040 3 Jan 2026
SPORTS

Ian Maksin: New Album Release Tour

 729 Fleming Street, Key West, FL, United States, Florida 33040 3 Jan 2026
MUSIC

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Upcoming New Year Events

Great Gatsby NYE 2026

 First Flight Island Restaurant & Brewery 31 Dec 2025
NEW-YEAR USD 269

New Year's Eve at Four Marlins

 1435 Simonton St, Key West, FL 33040 31 Dec 2025
NEW-YEAR

Terri white,Larry Baeder & friends

803 Emma St, Key West, FL 1 Jan 2026
MUSIC

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Upcoming Music Festivals Events

Put-in-Bay Days in Key West 2026

 Key West, Florida 11 Feb 2026
PARTIES

Mile 0 Fest Key West: Shane Smith and The Saints Casey Donahew & The Band of Heathens - Saturday

 Truman Waterfront Amphitheater 30 Jan 2026
FESTIVALS

Kaitlin Butts in Key West

 Truman Waterfront Park Amphitheater 29 Jan 2026
CONCERTS

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Trending Events in Key West

Key West M**der Mystery 2: A Deadly Dating Game!

 302 Fleming St 29 Nov 2025
TRIPS-ADVENTURES USD 10 TO 30

11th Annual Onesie Pub Crawl

 512 Greene St, Key West, FL 1 Feb 2026
PARTIES

Island Groove Pub Crawl - Chris is 60 and still rockin!

 22&Co Key West 10 Jan 2026
PARTIES

Jesse Rice’s “Party At The Pier House” Show

 Pier House Resort & Spa 7 Mar 2026
CONCERTS USD 36 TO 180

2026 Annual Southernmost Conch Republic POLAR PLUNGE

 Higgs Beach Key West, Florida 8 Feb 2026
CONTESTS

Scott Kirby- 35 Years of Songs & Stories

Key West Theater 26 Feb 2026
MUSIC

28th Annual Key West Half Marathon & Runfest

 Key West Historic Seaport 16 Jan 2026
MARATHONS

Scott Kirby- 35 Years of Songs & Stories

Key West Theater 2 Jan 2026
MUSIC

Murder Mystery Tea

 700 Fleming St, Key West, FL, United States, Florida 33040 7 Feb 2026
CONTESTS

🎶 Saturdays: Zach Lovering & Resident DJs at General Horseplay

 423 Caroline street, Key West, FL, United States, Florida 33040 3 Jan 2026
ART

CrossFit Mile Zero Cohen Weightlifting Seminar

 CrossFit Mile Zero 17 Jan 2026
SPORTS USD 82

First Sunday Open Mic Monthly Reading

327 Elizabeth St., Key West, Florida 33040 4 Jan 2026
OPEN-MIC

Release and Renew Ceremony at the Beach

 Higgs Beach Key West, Florida 2 Jan 2026

Author Talk with Michael Grunwald

 700 Fleming Street, Key West, FL, United States, Florida 33040 16 Jan 2026
ART

Key west 2026: Free 21 days of Spiritual Meditation for Peace

 Virtual 24 Jan 2026
MEDITATION FREE

More things to do in Key West

Live Music
Festivals
Comedy
Food & Drinks
New Year
Bar Crawls
Music Festivals
Halloween
Fireworks
Speed Dating
Pop-Ups