Festivals in Key West

Check out happening festivals events all around Key West, FL

The Greeen House Presents: Party In The Park with Just a Few Friends

 Sun, 31 Aug at 05:00 pm Truman Waterfront Park

Key West Brewfest Grand Tasting!

 Sat, 30 Aug at 05:00 pm Southernmost Beach Resort

Second Line Memorial Walking Parade

 Sun, 31 Aug at 05:00 pm 100 Duval St, Key West, FL 33040-6506, United States

Artisan Market @ the Party in the Park - Just a Few Friends

 Sun, 31 Aug at 05:30 pm Truman Waterfront Park

2025 Fantasy Fest Parade Viewing Party @ First Flight

 Sat, 25 Oct at 06:00 pm First Flight Island Restaurant & Brewery USD 177 to 212

Parrots & Margaritas 5K

 Sat, 30 Aug at 08:00 am 211 Duval St

Back to the Island Beach Party

 Sat, 30 Aug at 11:00 am 801 Duval St, Key West, FL 33040-7405, United States

Just a Few Friends Celebration, Key West

 Fri, 29 Aug at 08:00 am Key West

Brews & Bites: A 4-Course Paired Experience

 Fri, 29 Aug at 07:00 pm First Flight Island Restaurant & Brewery USD 97

Fins Up! Pool Party!!

Sat, 30 Aug at 01:00 pm 2001 S Roosevelt Blvd, Key West, FL 33040-5243, United States

New Moon Drum Circle

 Sat, 23 Aug at 07:00 pm 3128 N. Roosevelt Blvd., Key West, FL, United States, Florida 33040

Meet Up at the Chart Room

Thu, 28 Aug at 06:00 pm Chart Room

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

Rum & Sun Pool Party

 Sun, 17 Aug at 12:00 pm 3420 N. Roosevelt Blvd. , 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

Pencil Thin Mustache Contest

 Mon, 01 Sep at 02:00 pm Pier House Resort & Spa

Volunteer Meeting

 Mon, 25 Aug at 06:00 pm 319 Duval Street. Key West, FL 33040

Key West's Favorite Son City Proclamation

 Fri, 29 Aug at 11:00 am Shrimp Boat Sounds (Jimmy Buffetts Recording Studio)

Ultimate Friends Emerald Real Deal Reveal (INVITE ONLY)

 Sun, 31 Aug at 12:00 pm Emeralds International LLC

Volunteer Party for Floyd PEPA Jenkins for Fantasy Fest King 2025

 Mon, 18 Aug at 05:00 pm 618 Duval St, Key West, FL 33040-6555, United States

Jimmy Buffett Second Line Parade - Walk with Reef Relief

 Sun, 31 Aug at 04:15 pm 631 Greene St, Key West, FL, United States, Florida 33040

"A Labor Day Weekend Show!" Don Middlebrook, 3 BIG Nights @Key West, FL

 Fri, 29 Aug at 09:00 pm Jimmy Buffets Margaritaville Key West Flordia

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

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

Costume Swap and Sale!

Sat, 23 Aug at 10:00 am The Greeen House

Bark & Brew - Kickoff!

 Thu, 28 Aug at 05:00 pm 5950 Peninsular Avenue, Key West, FL, United States, Florida 33040

Pool Floatie Chug & Race

 Thu, 28 Aug at 01:00 pm Southernmost Beach Resort

October's Community Swim

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

Fantasy Fest 5K Run/Walk

 Mon, 20 Oct at 06:00 pm Duval Street

Shoreline Sessions Reggae Beach Festival

Sat, 01 Nov at 04:00 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

Phil Collins Experience at Key West Theater

Mon, 26 Jan at 08:00 pm 512 Eaton St, 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

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

Take Back The Night 2025

 Wed, 01 Oct at 06:30 pm Bayview Park

Melon Jelly LIVE @ The Alamo, Key West FL 🎶

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

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

Kash'd Out at Key West Theater

 Fri, 16 Jan Key West Theater

Farm Open House

 Sun, 26 Oct at 01:00 pm Monroe County Sheriff's Office Animal Farm

Sloppy Joe's Slumber Party

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

Famer's Market Mingle at the Truman Waterfront Farmers Market (sunset at 7:51 pm)

 Thu, 28 Aug at 02:00 pm Truman Waterfront Park

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

Just a Few Friends: Early Bird Clean Up at the Historic Waterfront

 Fri, 29 Aug at 08:00 am Reef Relief

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

Put-in-Bay Days in Key West 2026

 Wed, 11 Feb at 03:00 pm Key West, Florida

Fantasy Fest 2025 Bedtime Stories & Magical Monsters

 Fri, 17 Oct at 12:00 pm Key West, Florida

2025 float and parade entry theme is Captain Tony's Slumber Party and Bedtime Stories

 Sat, 25 Oct at 06:00 pm Truman Annex

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 in October!

 Sun, 19 Oct at 05:30 pm Sloppy Joe's Bar

AG at Sloppy Joes Key West Aug 27-Sept 2!

 Wed, 27 Aug at 10:00 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