Key West Events Calendar

From annual festivals to holiday celebrations, the fun never stops in Key West. We're looking forward to these upcoming Key West events. For details on any event or planning a holiday vacation, contact our local team! We're happy to provide nearby vacation rental recommendations and the inside scoop on all things Key West. 

barney

Weinerpalooza

Jan 19 2025 - 11:00am
January 18 Key West Weinerpalooza Website Key West's annual Dachshund Parade takes place Saturday, Jan. 18. All parade revelers are to gather at 11:30 a.m. in front of Customs House, 281 Front St., for a group portrait followed by the parade at 12 noon. Tails...Read more
Upcoming Events
kingfish mayhem

Kingfish Mayhem

Jan 15 2025 - 7:00am to Jan 19 2025 - 8:00pm
January 15 - 19, 2025 Key West Key West Kingfish Mayhem Website Angling teams targeting kingfish can vie for mastery and substantial cash prizes during the 2025 Key West Kingfish Mayhem tournament. The open division team that weighs in the heaviest kingfish, also known as...Read more
Upcoming Events
key west half marathon

Key West Half Marathon & Runfest Weekend

Jan 16 2025 - 7:00am to Jan 20 2025 - 5:00pm
The Annual Key West Half Marathon & 5k is a "bucket list" race.Read more
Races
southernmost regatta

The Southernmost Regatta

Jan 20 2025 - 7:00am to Jan 25 2025 - 7:00pm
January 20 - 25, 2025 Key West The Southernmost Regatta Website Top sailing teams from around the world compete in the azure waters off Key West, showcasing colorful sails and avid sportsmanship during five consecutive days of racing. Competition is open to One Design and...Read more
Upcoming Events
mile 0 fest

Mile 0 Fest

Jan 21 2025 - 7:00am to Jan 25 2025 - 11:00pm
Mile 0 Fest Key West is a new music festival considered a "must see" in the burgeoning Red Dirt & Americana music scene.Read more
Festivals
kelly mcgillis flag football

Kelly McGillis Classic International Flag Football Championships

Jan 21 2025 - 8:00am to Jan 27 2025 - 11:00pm
January 21 - 27, 2025 Key West Kelly McGillis Classic International Flag Football Championship Website Women from countries far and wide will be descending upon Key West for the 32nd annual flag football competition with teams participating from USA, Morocco, Spain, Mexico, Sweden, Pakistan, Mexico,...Read more
Upcoming Events
polar plunge

Conch Republic Polar Plunge

Feb 9 2025 - 12:00pm
February 09 Key West Conch Republic Polar Plunge Website All brave souls are welcome for the 15th Annual Southernmost Conch Republic Polar Plunge, a cherished tradition benefiting the programs of Samuel’s House supporting the homeless in Key West. Take the plunge into the cool Atlantic...Read more
Upcoming Events
Florida Keys Seafood Festival

Florida Keys Seafood Festival

Feb 15 2025 - 11:00am to Feb 16 2025 - 8:00pm
February 15 - 16, 2025 Key West Florida Keys Seafood Festival Website The 19th annual Florida Keys Seafood Festival takes place Saturday from 11 a.m. to 8 p.m. and Sunday from 11 a.m. to 5 p.m. at Truman Waterfront Park, located at the end of...Read more
Festivals

KEY WEST ART & CRAFT FESTIVAL

Feb 22 2025 - 8:15am to Feb 23 2025 - 10:15pm
February 22 - 23, 2025 Key West Key West Art & Craft Festival Website The Key West Craft Show and Old Island Days Art Festival are now combined to create the Key West Art & Craft Festival. The event includes artist demonstrations, a patron comfort...Read more
Upcoming Events
conch shell blowing contest

ANNUAL CONCH SHELL BLOWING CONTEST

Mar 8 2025 - 10:00am
March 08 Key West Conch Shell Blowing Contest Website An island tradition, this unique contest celebrates the historic importance of conch in the Keys and features contestants in several age categories attempting to make "music" with fluted conch shells. The contest takes place in the...Read more
Upcoming Events

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