Explore Key West

Happening Next in Key West

Upcoming Live Music Events

5th Annual Party Like A Rockstar Party

The Key West Empourium 21 Oct 2026
ENTERTAINMENT

A Green Parrot Beatle Tribute

 The Green Parrot 19 Oct 2026
ENTERTAINMENT

VIVA'S GRAND FINALE - FANTASY FEST PARADE VIEWING & DINNER PARTY

 Viva Argentinian Steakhouse 24 Oct 2026
FITNESS USD 86 TO 168

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Upcoming Festivals Events

Deep Eddy Vodka 2026 Fantasy Fest Parade

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

Captain Morgan's Masquerade March

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

Key West Fantasy Fest 2026

 Key West, Florida 16 Oct 2026
FESTIVALS

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Upcoming Food & Drinks Events

Nine One Five's Fantasy Fest Parade Viewing Party

 Nine One Five 24 Oct 2026
FITNESS USD 59

Key West Powerboat Races 2026 - VIP Tent - FRIDAY

 Sunset Pier 6 Nov 2026
SPORTS USD 525

Party Like a Rockstar

319 Duval St, Key West, FL 24 Oct 2026
FOOD-DRINKS

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Upcoming Trick Or Treat Events

The Fright Crawl | Key West Halloween Bar Crawl 2026 | Thurs, Oct. 29

 TBA 29 Oct 2026
FITNESS USD 8 TO 71

Halloween Bar Crawl 10/31 - KEY WEST

 La Concha Key West, Autograph Collection 31 Oct 2026
FITNESS USD 20 TO 25

Halloween Eve Bar Crawl 10/30 - KEY WEST

 La Concha Key West, Autograph Collection 30 Oct 2026
FITNESS USD 20 TO 25

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Upcoming Bar Crawls Events

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

 TBA 31 Oct 2026
FITNESS USD 8 TO 82

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

 TBA 31 Oct 2026
FITNESS USD 8 TO 71

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

 TBA 30 Oct 2026
FITNESS USD 8 TO 71

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Upcoming Comedy Events

Illusions The Drag Queen Show Key West - Drag Queen Show - Key West, FL

 Illusions the Drag Queen Show Key West 21 Aug 2026
FITNESS USD 13 TO 914

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

 Key West Theatre 14 Nov 2026
COMEDY

Muscle Men Male Strippers Revue & Male Strip Club Shows Key West FL

 Muscle Men Male Strippers Key West 23 Oct 2026
FITNESS USD 13 TO 914

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Upcoming Carnivals Events

Fantasy Fest Street Fair & Costume Promenade

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

Asylum Circus Haunted House for all ages!

1908 Flagler Ave., Key West, FL 30 Oct 2026
GHOST-HUNTS

Children's Day

 Bayview Park Key West 25 Oct 2026
ART

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Upcoming Boat Parties Events

Fantasy Sunsets Vip Yacht Experience

 The Perry Hotel & Marina Key West 16 Oct 2026
FITNESS USD 227

Key West Lighted Boat Parade

 0 Duval Street, Key West, FL, United States, Florida 33040 12 Dec 2026
PARADES

Christmas Day Brunch

 S/V Argo Navis 25 Dec 2026
BRUNCH

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Trending Events in Key West

Key West Murder Mystery 2: Crime on Date Night!

 502 Whitehead St, Key West 1 Nov 2026
TRIPS-ADVENTURES USD 15

LUV2GLOW - LIQUID FREQUENCY - FANTASY FEST 2026 at Rick's Key West

 Rick's Bar 21 Oct 2026
FITNESS USD 36 TO 117

2026 Fantasy Fest Parade Viewing Party @ First Flight

 First Flight Island Restaurant & Brewery 24 Oct 2026
PARADES USD 177 TO 562

"The Fat Lady Sings" Tea Dance

 La Te Da 25 Oct 2026
FESTIVALS

Paparazzi Row Block Party

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

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
FESTIVALS

Key West Powerboat Races 2026 - VIP Tent - SUNDAY

 Sunset Pier 8 Nov 2026
FITNESS USD 525

VIP Parade Viewing Party At The New Smokin Tuna!

 Smokin' Tuna Saloon 24 Oct 2026
PARADES

Garrison Keillor & Erica Rhodes

 Key West Theater 27 Oct 2026
ART

Sloppy Joe's 47th Annual Toga Party

 Sloppy Joe's Key West 22 Oct 2026
CONTESTS

33rd Annual Homemade Bikini Contest

 Irish Kevin's 21 Oct 2026
FITNESS USD 23 TO 1,069

Southernmost Scavenger Hunt's 7th Annual Fantasy Fest Bar Crawl

 Conch Republic Seafood Company 22 Oct 2026
FESTIVALS

Southernmost Slow Riders in the Fantasy Fest parade

Truman Annex 24 Oct 2026
PARTIES

GOT A BIG HEAD? PROVE IT!

 Coffee Butler Amphitheater 22 Oct 2026
ART

Cocktails for Animal Tails - A Fantasy Fest Party!

 Rick's Key West 20 Oct 2026
PARTIES
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More things to do in Key West

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Trunk Or Treat
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