The Fright Crawl | Key West's #1 Halloween Bar Crawl 2026 | Sat, Oct 31 Sat, 31 Oct at 07:30 pm TBA USD 8 TO 82 FITNESS
Key West Powerboat Races 2026 - General Admission - Fri Fri, 06 Nov at 09:00 am Sunset Pier USD 75 FITNESS
Key West Powerboat Races 2026 - VIP Tent - FRIDAY Fri, 06 Nov at 09:00 am Sunset Pier USD 525 FITNESS
Duval Street Block Party Presented by Keystar Construction Fri, 06 Nov at 06:00 pm Duval St, Key West, FL 33040, United States SPORTS
Key West Powerboat Races 2026 - VIP Tent - SUNDAY Sun, 08 Nov at 09:00 am Sunset Pier USD 525 FITNESS
Candlelight: Coldplay vs. Imagine Dragons Fri, 13 Nov at 06:00 pm Key West Theater USD 40 TO 85 CANDLELIGHT-CONCERTS
Mangoes Drag Brunch Royale Halloween Edition Sun, 01 Nov at 11:30 am Mangoes Restaurant USD 55 TO 66 FITNESS
Key West Oyster Fest 2026: A Benefit for the Oyster Sat, 14 Nov at 05:00 pm 231 Margaret St, Key West, FL, United States, Florida 33040 MUSIC
Key West Powerboat Races 2026 - General Admission - Sun Sun, 08 Nov at 09:00 am Sunset Pier USD 75 FITNESS
Official Racer's Party at Hogs Breath Saloon presented by Good Boy Vodka Thu, 05 Nov at 07:30 pm Hog's Breath Saloon SPORTS
A Tribute to the Songs of Pete & Wayne with Pete Jarvis, Larry Strickland, Ray Fogg & Special Guests Sat, 14 Nov at 08:00 pm Key West Theatre COMEDY
Candlelight: The Best of Hans Zimmer Fri, 13 Nov at 08:30 pm Key West Theater USD 44 TO 102 ENTERTAINMENT
Gold Pool Parties Sun, 20 Sep 1129 Fleming St, Key West, FL, United States, Florida 33040 POOL-PARTIES
34rd Annual ABC 10K/5K Run/Walk Sat, 07 Nov at 07:30 am 1000 Atlantic Blvd, Key West, FL 33040-4852, United States SPORTS
Key West 11th Annual Casino Night by SOS Foundation Fri, 13 Nov at 06:30 pm Casa Marina Key West, Curio Collection by Hilton USD 18 TO 135 NONPROFIT
Illusions The Drag Queen Show Key West - Drag Queen Show - Key West, FL Fri, 22 Apr at 07:00 pm Illusions the Drag Queen Show Key West USD 13 TO 914 FITNESS
IAN MAKSIN in KEY WEST: "SONGS of LOVE & PEACE" 2026 Concert Tour Wed, 11 Nov at 07:30 pm Congregation B'nai Zion USD 18 TO 29 FITNESS
Tiki House Party presented by Key West First Legal Rum Tue, 03 Nov at 05:30 pm Tiki House Key West SPORTS
Buccaneer Booty's been Burgled from Key West Outdoor Exploration Game Sun, 01 Nov at 12:00 am Key West Aquarium USD 13 TRIPS-ADVENTURES
Full Moon Magic Ghost Stories Mon, 26 Oct 1319 Duval Street, Key West, FL, United States, Florida 33040 GHOST-HUNTS
The Lighting of the "Harbor Walk of Lights" Wed, 25 Nov at 05:00 pm Conch Republic Seafood Company HOLIDAY
Sea Turtle Shell-ebration with Save-A-Turtle in the Florida Keys! Sat, 14 Nov at 06:00 pm Key West Aquarium USD 0 TO 13 FITNESS
Custom House Holiday Concert & Bazaar Fri, 11 Dec at 05:00 pm Key West Art & Historical Society MUSIC
Powerboat Village in the Historic Seaport! Wed, 04 Nov at 11:30 am Conch Republic Seafood Company SPORTS
Candlelight: Vivaldi's Four Seasons Fri, 11 Dec at 06:00 pm Key West Theater USD 40 TO 88 CANDLELIGHT-CONCERTS
32nd Annual Hog's Breath Saloon Hog Trot 5K Sat, 28 Nov at 08:00 am 400 Front St, Key West, FL, United States, Florida 33040 SPORTS
80s & 90s Trivia Night! Sun, 01 Nov at 07:00 pm 126 Simonton Street, Key West, FL, United States, Florida 33040
Key West Murder Mystery 2: Crime on Date Night! Sun, 01 Nov at 12:00 am 502 Whitehead St, Key West USD 15 TRIPS-ADVENTURES
Dinner with Entrepreneurs: Small Town, Small Business Edition | Key West Sat, 31 Oct Restaurant of the Week USD 29 TO 55 BUSINESS
Candlelight: Tribute to Fleetwood Mac Fri, 11 Dec at 08:30 pm Key West Theater USD 44 TO 85 CANDLELIGHT-CONCERTS
Mangoes Drag Brunch Royale Christmas Show Sun, 20 Dec at 11:30 am Mangoes Restaurant USD 55 TO 66 FITNESS
29th Annual Key West Half Marathon & Runfest Fri, 15 Jan at 04:00 pm Key West Historic Seaport MARATHONS
"Welcome Back" Season Kick-off Party! Fri, 06 Nov at 05:30 pm 720 Caroline Street, Key West, FL, United States, Florida 33040 ENTERTAINMENT
Key West, FL Roadshow- A free, Five Day Only Buying Event Tue, 03 Nov Hilton Garden Inn Key West / The Keys Collection FREE FITNESS
Holidays Makers Market Sat, 28 Nov at 10:00 am 533 Eaton St, Key West, FL, United States, Florida 33040 ART
Stetson and Bethune Cookman Baseball in Key West Sat, 14 Nov at 07:00 pm Rex Weech Field USD 18 TO 500 FITNESS
"Of Course Dave" live DJing Sat, 07 Nov at 07:00 pm 126 Simonton Street, Key West, FL, United States, Florida 33040 WORKSHOPS
Trivia Night Wed, 04 Nov at 06:00 pm 1319 Duval Street, Key West, FL, United States, Florida 33040 FESTIVALS
Autumn Pairings: An Evening at the Mansion Wed, 18 Nov at 06:00 pm George's | Café • Bar • Spritz USD 117 FITNESS
Green Parrot Bar 🍻 CHARITY BINGO NIGHT! 🍻 Featuring Irreverent Warriors Key West🇺🇸 Mon, 30 Nov at 07:00 pm The Green Parrot NONPROFIT
Industry Night Tue, 03 Nov at 02:00 pm 126 Simonton Street, Key West, FL, United States, Florida 33040
Candlelight: Christmas Classics Sat, 26 Dec at 04:30 pm Key West Theater USD 40 TO 76 CANDLELIGHT-CONCERTS
Copy of Seattle Hidden Gems Experience Tue, 28 Jul at 10:00 am Mallory Square USD 23 TRIPS-ADVENTURES
Santa at the Key West Cooking Show Sun, 13 Dec at 01:00 pm 291 Front St suite 207, Key West, FL, United States, Florida 33040 KIDS
Night of Poe - Key West, FL Fri, 27 Nov at 06:00 pm Key West Theater and Community Stage USD 59 TO 86
The Broken Hearts: A Tribute to Tom Petty & The Heartbreakers Sat, 12 Dec at 08:00 pm Key West Theater MUSIC
Taste of Key West 2027! Mon, 05 Apr at 06:00 pm Truman Waterfront, Key West, FL, United States, Florida 33040 HEALTH-WELLNESS
An Evening Aglow: A Candlelight Christmas with Marjory Lee Tue, 15 Dec at 08:00 pm Key West Theater MUSIC
December Duo Holiday Concert: Irie Monte and Crispin Campbell Sat, 12 Dec at 06:00 pm 533 Eaton St, Key West, FL, United States, Florida 33040 ENTERTAINMENT
CFK Community Day 2026 Sat, 07 Nov at 10:00 am 5901 College Rd, Key West, FL 33040-4315, United States ART
SILKIES HIKE - IRREVERENT WARRIORS KEY WEST - 12.12.26 Sat, 12 Dec at 11:00 am 21 E Quay Rd, Key West, FL 33040, United States SPORTS
Pirates & Mermaids Rum Chase Sat, 21 Nov at 05:00 pm 5210 College Rd, Key West, FL, United States, Florida 33040 CONTESTS
One Piece TCG - Thursday Night League! Thu, 05 Nov at 04:00 pm 2506 N Roosevelt Blvd, Suite 101, Key West, FL, United States, Florida 33040 SPORTS
Kristen McNamara: Stories & Songs - Live Recording at the Key West Theater Sat, 21 Nov at 07:00 pm Key West Theater MUSIC
Yoga Nidra + Sound Bath with Malaika Sun, 01 Nov at 04:00 pm 612 Fleming Street, Key West, FL, United States, Florida 33040 HEALTH-WELLNESS