Upcoming Live Music Events

Mac McAnally in Key West

 Key West Theater 5 Dec 2025
CONCERTS

Buffett Through The Years

 512 Eaton St, Key West, FL, United States, Florida 33040 31 Oct 2025
CONCERTS

Mac McAnally in Key West

 Key West Theater 6 Dec 2025
CONCERTS

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Upcoming Festivals Events

Fantasy Fest 5K Run/Walk

 Duval Street 20 Oct 2025
MARATHONS

Aqua Idol ~ Royal Edition "Floyd PEPA Jenkins for Fantasy Fest KING 2025

 AquaPlex Key West 23 Sep 2025
FESTIVALS

The Fabulous Spectrelles

 Kaya Island Eats 3 Oct 2025
FESTIVALS

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Upcoming Comedy Events

Murder at the Hard Rock Cafe

 Hard Rock Cafe Key West 9 Oct 2025

Peter Antoniou "Psychic" Comedian

 512 Eaton St, Key West, FL, United States, Florida 33040 11 Oct 2025
COMEDY

Puddles Pity Party at Key West Theater

 Key West 28 Sep 2025
ENTERTAINMENT

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Upcoming Food & Drinks Events

Key West Powerboat Races 2025 - VIP Tent - SUNDAY

 Sunset Pier 9 Nov 2025
SPORTS USD 461 TO 518

Truman Waterfront Farmers Market

 21 E Quay Rd, Key West, FL, United States, Florida 33040 11 Sep 2025
FARMERS-MARKETS

Farm Open House

 Monroe County Sheriff's Office Animal Farm 14 Sep 2025
NONPROFIT

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Upcoming Carnivals Events

LUV2GLOW - VIVID DREAMS - FANTASY FEST 2025 @Rick's Key West

 Rick's Bar 22 Oct 2025
FESTIVALS USD 36 TO 117

Sloppy Joe's 46th Annual Toga Party

 Sloppy Joe's 23 Oct 2025
ENTERTAINMENT

Sloppy Joe's Slumber Party

 Sloppy Joe's 22 Oct 2025
PARTIES

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Upcoming Parades Events

2025 Fantasy Fest Parade Viewing Party @ First Flight

 First Flight Island Restaurant & Brewery 25 Oct 2025
FESTIVALS USD 177 TO 212

Captain Morgan's Masquerade March

 Fleming St, Key West, FL 33040, United States 24 Oct 2025
PARTIES

2026 Annual Southernmost Conch Republic POLAR PLUNGE

 Higgs Beach Key West, Florida 8 Feb 2026
CONTESTS

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Upcoming Halloween Events

Key West Halloween Drag Brunch Royale

 Mangoes Restaurant 19 Oct 2025
BRUNCH USD 55 TO 71

2025 - Friday, Oct. 31 - Jerry Diaz's Sunset Cruise in Key West!

 Sebago Key West 31 Oct 2025

Early Bird Clean Up Duval and Virginia hosted by Realty ONE Group (The Halloween edition)

 Realty ONE Group Destination 31 Oct 2025
HALLOWEEN

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Trending Events in Key West

Oktoberfest - 2 Year Anniversary!!

 5635 1st ave, Key West, FL, United States, Florida 33040 13 Sep 2025
OKTOBERFEST

Oktoberfest

 Sunset Lounge Sigsbee 26 Sep 2025
OKTOBERFEST

Key West 10th Annual Casino Night by SOS Foundation

 Beachside Resort & Residences Key West 14 Nov 2025
NONPROFIT USD 18 TO 135

Clay Walker @ Country Music Cruise in Key West

 Country Music Cruise 29 Oct 2025
COUNTRY-MUSIC-FESTIVALS

Key West Powerboat Races 2025 - General Admission - Fri

 Sunset Pier 7 Nov 2025
SPORTS USD 71 TO 105

Pajama And Lingerie Party

 Aqua Bar and Nightclub, Duval Street, Key West, FL, USA 23 Oct 2025
PARTIES USD 30 TO 115

2025 KWPD Love Fund Annual Ball

Opal Key Resort & Marina 20 Sep 2025

September's Community Swim Night

 1319 Duval Street, Key West, FL, United States, Florida 33040 20 Sep 2025
MUSIC

Bingo Sunday with Qmitch ~ This one is all Floyd

 22 Bingo 14 Sep 2025
BINGO

Tay Tay Tuesday - In Your Wildest Dreams

 Sunset Pier ~ Key West 21 Oct 2025
CONCERTS

Peter Antoniou at Key West Theater

 Key West 11 Oct 2025
PERFORMANCES

Service Industry Night at Mary Ellen's

 420 Appelrouth Lane, Key West, FL, United States, Florida 33040 7 Sep 2025

Peter Antoniou

 Key West Theater 10 Oct 2025
CONTESTS

Puff N Paint Hibiscus on Canvas with Painting the Keys

 3128 N. Roosevelt Blvd., Key West, FL, United States, Florida 33040 13 Sep 2025
ART

Jukebox Wizard with Landon!

 420 Appelrouth Lane, Key West, FL, United States, Florida 33040 10 Sep 2025
ART

More things to do in Key West

Live Music
Festivals
Comedy
Food & Drinks
Carnivals
Parades
Halloween
Pop-Ups
Oktoberfest
Labor Day
Music Festivals
Candlelight Concerts