Festivals in Key West
Check out happening festivals events all around Key West, FL
2025 Fantasy Fest Parade Viewing Party @ First Flight
Sat, 25 Oct at 06:00 pm
First Flight Island Restaurant & Brewery
USD 177 to 212
Fantasy Fest 5K Run/Walk
Mon, 20 Oct at 06:00 pm
Duval Street
Aqua Idol ~ Royal Edition "Floyd PEPA Jenkins for Fantasy Fest KING 2025
Tue, 23 Sep at 06:00 pm
AquaPlex Key West
The Fabulous Spectrelles
Fri, 03 Oct at 08:00 pm
Kaya Island Eats
Shoreline Sessions Reggae Beach Festival
Sat, 01 Nov at 04:00 pm
1319 Duval Street, Key West, FL, United States, Florida 33040
Captain Morgan's Masquerade March
Fri, 24 Oct at 05:30 pm
Fleming St, Key West, FL 33040, United States
Key West Powerboat Races 2025 - Hot Tin Roof Balcony - SUNDAY
Sun, 09 Nov at 09:00 am
Hot Tin Roof Restaurant
USD 403 to 805
Mike Stack and Friends on the BIG stage at the Sunset Pier
Sat, 11 Oct at 05:30 pm
Sunset Pier ~ Key West
Oktoberfest - 2 Year Anniversary!!
Sat, 13 Sep at 02:00 pm
5635 1st ave, Key West, FL, United States, Florida 33040
The Fabulous Spectrelles
Fri, 12 Sep at 08:00 pm
Kaya Island Eats
The Fabulous Spectrelles
Fri, 19 Sep at 08:00 pm
Kaya Island Eats
61th Annual Key West Art & Craft Festival
Sat, 21 Feb at 10:00 am
Truman Waterfront Park
The Fabulous Spectrelles
Fri, 26 Sep at 08:00 pm
Kaya Island Eats
Melon Jelly LIVE @ The Alamo, Key West FL 🎶
Fri, 21 Nov at 09:00 pm
The Alamo Key West
22&Co Bingo Sundays w/Qmitch - Floyd for King
Sun, 14 Sep at 05:00 pm
22&Co
The Fabulous Spectrelles
Fri, 10 Oct at 08:00 pm
Kaya Island Eats
October's Community Swim
Sat, 11 Oct at 06:00 pm
1319 Duval Street, Key West, FL, United States, Florida 33040
25th Annual Living Art Expo
Fri, 24 Oct at 07:00 pm
0 Duval Street, Key West, FL, United States, Florida 33040
TuTu Tuesday 2025 - Tuesday Night Fever & Our Robot Friends
Tue, 21 Oct at 07:00 pm
423 Caroline street, Key West, FL, United States, Florida 33040
The 72-Hour Film Challenge at Williams Hall
Tue, 09 Sep at 06:00 pm
729 Fleming St, Key West, FL 33040-6827, United States
Key West Pet Masquerade 2025
Wed, 22 Oct at 05:00 pm
Key West Ampitheatre
Cupid's Chase 5K Key West
Sat, 14 Feb at 09:00 am
Clarence S.Higgs Memorial Beach
USD 45 to 50
Take Back The Night 2025
Wed, 01 Oct at 06:30 pm
Bayview Park
Monarch Fine Art Grand Opening Celebration
Fri, 24 Oct at 12:00 am
910 Duval Street, Key West, FL, United States, Florida 33040
Phil Collins Experience at Key West Theater
Mon, 26 Jan at 08:00 pm
512 Eaton St, Key West, FL, United States, Florida 33040
Changes In Latitude at Key West Theater
Tue, 03 Mar at 08:00 pm
512 Eaton St, Key West, FL, United States, Florida 33040
LUV2GLOW - VIVID DREAMS - FANTASY FEST 2025 @Rick's Key West
Wed, 22 Oct at 08:00 pm
Rick's Bar
USD 36 to 117
Sloppy Joe's 46th Annual Toga Party
Thu, 23 Oct at 08:00 pm
Sloppy Joe's
Post-Fest Plunge Ice Bath Social
Sun, 26 Oct at 02:00 pm
Kava Culture Key West
Cocktails for Animal Tails
Tue, 21 Oct at 08:00 pm
Rick's Bar
Sloppy Joe's Slumber Party
Wed, 22 Oct at 11:00 am
Sloppy Joe's
Aqua Idol ~ Royal Edition "Floyd PEPA Jenkins for Fantasy Fest KING 2025
Tue, 09 Sep at 06:00 pm
AquaPlex Key West
A Tribute to the Songs of Pat Dailey in Key West with Ray Fogg and Reese Dailey
Sat, 14 Feb at 08:00 pm
Key West Theatre
Aqua Idol ~ Royal Edition "Floyd PEPA Jenkins for Fantasy Fest KING 2025
Tue, 16 Sep at 06:00 pm
AquaPlex Key West
Kash'd Out at Key West Theater
Fri, 16 Jan at 08:00 pm
Key West Theater
Aqua Idol ~ Royal Edition "Floyd PEPA Jenkins for Fantasy Fest KING 2025
Tue, 30 Sep at 06:00 pm
AquaPlex Key West
Aqua Idol ~ Royal Edition "Floyd PEPA Jenkins for Fantasy Fest KING 2025
Tue, 07 Oct at 06:00 pm
AquaPlex Key West
Creative Hat Party
Fri, 17 Oct at 08:00 pm
Captain Tony's Saloon "Oldest Bar In Florida"
Fantasy Fest Duck, Duck, Booze Pool Party at Havana Cabana
Mon, 20 Oct at 12:00 pm
3420 N. Roosevelt Blvd. , Key West, FL, United States, Florida 33040
2025 - Friday, Oct. 31 - Jerry Diaz's Sunset Cruise in Key West!
Fri, 31 Oct at 05:00 pm
Sebago Key West
Berkshire Hathaway Parade of Homes Mega Open House Event
Thu, 23 Oct at 11:00 am
922 Caroline Street, Key West, FL, United States, Florida 33040
Crooks Second Line Parade
Sun, 15 Feb at 12:00 pm
111 Olivia St (temporary during construction), Key West, FL
THE BEATLE BAND EXTRAORDINAIRE! FANTASY FEST - 2025 GREEN PARROT
Mon, 20 Oct at 05:30 pm
Green Parrot Bar Key West
The Massacoustics at Key West Theater
Wed, 04 Feb at 08:00 pm
Key West Theater
FLORIDA KEYS COUNCIL OF THE ARTS FANTASY FEST POSTER SIGNING PARTY
Tue, 21 Oct at 03:00 pm
La Concha Key West
Fantasy Fest 2025 Bedtime Stories & Magical Monsters
Fri, 17 Oct at 12:00 pm
Key West, Florida
2025 Fantasy Fest Parade
Sat, 25 Oct at 06:00 pm
Truman Annex
Put-in-Bay Days in Key West 2026
Wed, 11 Feb at 03:00 pm
Key West, Florida
Early Bird Clean up Key West Firestation Lot on Simonton St hosted by Kenna Construction
Fri, 24 Oct at 08:00 am
Simonton Street City Parking Lot
Southernmost Turkey Trot 5K
Thu, 27 Nov at 08:00 am
The Southernmost Point Buoy
Key West Power Boat Races
Wed, 05 Nov at 08:30 am
Fury Water Adventures Key West
Midnight MAss Fantasy Fest
Fri, 24 Oct at 10:00 pm
Island House Key West Gay Hotel & Resort
Fantasy Fest
Sun, 26 Oct at 12:00 pm
Key West, Florida
AG at Fantasy Fest Sloppy Joes Key West!
Sun, 19 Oct at 05:30 pm
Sloppy Joe's Bar
RockHouse LIVE at Sloppy Joe's, Key West, FL!
Wed, 08 Oct at 10:00 pm
Sloppy Joes, Key West
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Festivals in Key West