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

31st Annual Taste of Key West

 Mon, 23 Mar at 06:00 pm Truman Waterfront, Key West, FL, United States, Florida 33040

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

Meghan Barter: Human Jukebox Release Concert + Listening Party

 Fri, 10 Oct at 07:00 pm Key West Theater

Mangoes 2025 Fantasy Fest Parade Party

 Sat, 25 Oct at 06:00 pm Mangoes Restaurant Key West

Captain Morgan's Masquerade March

 Fri, 24 Oct at 05:30 pm Fleming St, Key West, FL 33040, United States

Mike Stack and Friends on the BIG stage at the Sunset Pier

 Sat, 11 Oct at 05:30 pm Sunset Pier ~ Key West

Key West Pet Masquerade 2025

Wed, 22 Oct at 05:00 pm Key West Ampitheatre

DEADFEST KEY WEST - FALL SESSIONS - DEC 5th, 6th & 7th

 Fri, 05 Dec at 03:00 pm The Alamo Key West

25th Annual Living Art Expo

 Fri, 24 Oct at 07:00 pm 0 Duval Street, Key West, FL, United States, Florida 33040

Bangers and Mash at the Celtic Conch

 Sat, 25 Oct at 05:00 pm Celtic Conch Public House

Cocktails for Animal Tails

 Tue, 21 Oct at 08:00 pm Rick's Bar

Fantasy Fest Celebration

 Sat, 25 Oct at 12:00 pm 1000 Duval Street, Key West, FL, United States, Florida FL 33040

Sloppy Joe's 46th Annual Toga Party

 Thu, 23 Oct at 08:00 pm Sloppy Joe's

October's Community Swim

 Sat, 11 Oct at 06:00 pm 1319 Duval Street, Key West, FL, United States, Florida 33040

Shoreline Sessions Reggae Beach Festival

Sat, 01 Nov at 04:00 pm 1319 Duval Street, Key West, FL, United States, Florida 33040

The Bedtime Bizarre at Blue Flamingo Resort

 Wed, 22 Oct at 06:00 pm Blue Flamingo Resort Key West

The Fabulous Spectrelles

 Fri, 10 Oct at 08:00 pm Kaya Island Eats

Adult Costume Swap & Sale- Last Chance before Fantasy Fest!

 Sat, 11 Oct at 10:00 am 3128 N. Roosevelt Blvd., Key West, FL, United States, Florida 33040

Post-Fest Plunge Ice Bath Social

 Sun, 26 Oct at 02:00 pm Kava Culture Key West

Wheeland Brothers

 Sat, 08 Nov at 08:00 pm Key West Theater

61th Annual Key West Art & Craft Festival

 Sat, 21 Feb at 10:00 am Truman Waterfront Park

Oktoberfest Key West

 Fri, 10 Oct at 11:00 am 522 FRONT ST, Key West, FL, United States, Florida 33040

"The Fat Lady Sings" Tea Dance

 Sun, 26 Oct at 04:00 pm La Te Da

Wesley House Holiday Village & Bike Ride

 Fri, 05 Dec at 05:00 pm Coffee Butler Amphitheater

Fantasy Fest 5K Run/Walk

 Mon, 20 Oct at 06:00 pm Duval Street

Freedom Flotilla Festival

 Fri, 19 Dec at 05:00 pm Key West, Floirda

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

On Our Way To Paddy's Day Weekend Celebration!

Thu, 09 Oct at 07:00 pm 528 Front Street, Key West, FL, United States, Florida 33040

Costume Swap & Sale!

 Sat, 11 Oct at 10:00 am The Greeen House

LET'S GET LOONEY! FANTASY FEST AFTER PARADE PARTY!

 Sat, 25 Oct at 10:00 pm 420 Appelrouth Lane, Key West, FL, United States, Florida 33040

Creative Hat Party

 Fri, 17 Oct at 08:00 pm Captain Tony's Saloon "Oldest Bar In Florida"

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, 07 Oct at 06:00 pm AquaPlex Key West

Mermaid Mayhem at the Blue Flamingo Resort

 Sat, 18 Oct at 12:00 pm Blue Flamingo Resort 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

Bangers and Mash Gig at the Celtic Conch

 Fri, 24 Oct at 05:00 pm Celtic Conch Public House

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

 Wed, 22 Oct at 08:00 pm Rick's Bar USD 36 to 117

Key West Fantasy Fest 2025

 Sat, 25 Oct at 09:00 am Sunset Pier USD 88

Freedom Flotilla Festival

 Fri, 19 Dec at 05:00 pm Key West Free

The Greeen House Costume Swap & Sale with Hoebee Live Remote

 Sat, 11 Oct at 10:00 am 3128 N Roosevelt Blvd, Key West, FL 33040-4113, United States

Melon Jelly LIVE @ The Alamo, Key West FL 🎶

 Fri, 21 Nov at 09:00 pm The Alamo Key West

Monarch Fine Art Grand Opening Celebration

 Fri, 24 Oct at 12:00 am 910 Duval Street, Key West, FL, United States, Florida 33040

Cupid's Chase 5K Key West

 Sat, 14 Feb at 09:00 am Clarence S.Higgs Memorial Beach USD 45 to 50

Harvest Festival

 Thu, 09 Oct at 04:00 pm Sigsbee Community Center

Funk It Up Party

 Thu, 23 Oct at 05:30 pm 922 Caroline Street, Key West, FL, United States, Florida 33040

Sloppy Joe's Slumber Party

 Wed, 22 Oct at 11:00 am Sloppy Joe's

Bahama Village Goombay Festival

 Fri, 17 Oct at 12:00 pm Petronia St, Key West, FL 33040, United States

Hangover Pool Party at Havana Cabana

 Sun, 26 Oct at 12:00 pm 3420 N. Roosevelt Blvd. , Key West, FL, United States, Florida 33040

Golf Cart Facade Viewing Tour Fantasy Fest

 Wed, 29 Oct at 06:30 pm 3128 N. Roosevelt Blvd., Key West, FL, United States, Florida 33040

Bangers and Mash gig at The Celtic Conch

 Thu, 23 Oct at 05:00 pm Celtic Conch Public House

Martini Monday at Virgilio's

Mon, 20 Oct at 06:00 pm Virgilio's

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

CHANNEL 3 AND REGGAE LOU & THE KIND BUDZ REHAB POOL PARTY

 Sun, 26 Oct at 02:00 pm 200 William St, Key West, FL, United States, Florida 33040

FANTASY FEST. STREET FAIR

 Fri, 24 Oct at 05:00 am Duval Street, Key West

The Carole King & James Taylor Story ft. Phoebe Katis & Dan Clews

 Tue, 25 Nov at 08:00 pm Key West Theater

LES GREEENE & THE SWAYZEES PAJAMA POOL PARTY TAKE 2 AT THE MARKER!

 Thu, 23 Oct at 02:00 pm 200 William St, Key West, FL, United States, Florida 33040

FANTASY FEST. STREET FAIR

 Sat, 01 Nov at 04:00 am 700 Duval St, Key West, FL 33040-7404, United States

Fantasy Fest 2025 Annual Competitive Bar Crawl Sponsored by Dulce Vida Tequila!

 Thu, 23 Oct at 02:00 pm 631 Greene St, Key West, FL 33040-6624, United States

Bare As You Dare Farewell Party

 Sun, 26 Oct at 05:00 pm Captain Tony's Saloon Key West

Midnight MAss Fantasy Fest

 Fri, 24 Oct at 10:00 pm Island House Key West Gay Hotel & Resort

Key West 250th Celebration and Time Capsule Opening 2072

 Wed, 25 Mar at 09:15 am Mallory Square Key West

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

Krewe de Krazy Life Meet and Greet

 Sun, 19 Oct at 12:00 pm Galleon Tiki Bar

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

Early Bird Clean up KW Firestation Lot on Simonton St hosted by Kenna Construction & ShineGroup, eXp

 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

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

Party in Plaid

 Tue, 21 Oct at 08:00 pm Captain Tony's Saloon Key West

RockHouse LIVE at Sloppy Joe's, Key West, FL!

 Wed, 08 Oct at 10:00 pm Sloppy Joes, Key West