21st Annual Earth Day 5k
McCoy Indigenous Park 1801 White St, Key West, FL, United StatesThe 21st Annual Earth Day 5k Run/Walk is coming up! There will be Earth Friendly Recyclable Awards for the top overall male & female, top [...]
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20th Annual Key West Paddle Classic
Lazy Dog Adventures 5114 Overseas Hwy, Key West, FL, United States Join in on this weekend of fun at the 20th Annual Key West Paddle Classic and paddle around the island with your friends and [...]
Mile-High Key Lime Pie Eatin’ Contest
Register if you think you can devour a 9" Key Lime Pie topped with a mountain of whipped cream faster than the competition. This world [...]
24th Annual Battle of the Bars
Schooner Wharf Bar 202 William St, Key West, FL, United States"A day of beers, bartenders, margaritas and mayhem helps to dramatically improve the lives of local residents and local causes – only in Key West. [...]
$35
Southernmost Marathon & Half
 *More information coming soon! Race info Course maps  Â
37th Annual Key West Super Boat World Championship
Truman Waterfront 202 Southard Street, Key West, United States Schedule of events: superboat.com/schedule *More information soon
33rd Annual Schooner Wharf Bar Wrecker’s Cup Race Series
Schooner Wharf Bar 202 William St, Key West, FL, United StatesSchooner Wharf Bar is hosting the first of four races during their Annual Wrecker’s Cup Race Series. The course is 7 miles from Key West [...]
37th Annual 7-Mile Bridge Run
The 7-Mile Bridge Run is put together by the Marathon Runners Club and is the only known run that is completely surrounded by water from [...]
Mile High Key Lime Pie Eatin’ Contest
Sunset Pier at Ocean Key Resort & Spa 0 Duval Street, Key West, FloridaDo you think you could devour a 9″ Key Lime Pie topped with a mountain of whipped cream faster than the competition? Then register for [...]
Hemingway 5K Sunset Run & Paddleboard Race
As part of Hemingway Days, a six-day event that commemorates the life of Ernest Hemingway who lived and wrote in Key West during the 1930s, [...]
Annual 7-Mile Bridge Run 2019
7-Mile BridgeThe 7-Mile Bridge Run is put together by the Marathon Runners Club and is the only known run that is completely surrounded by water from [...]
$75
Annual Cow Key Channel Run
Cow Key Channel Bridge Cow Key Channel Bridge, Key West, FL, United StatesDo you feel like running across a bridge in the Florida Keys without waking up early or breaking a sweat? This 300-foot mock marathon over the [...]
$10
Zonta ABC 5K/10K
Salute on Higgs Beach 1000 Atlantic Blvd, Key West, FL, United StatesBenefiting women’s health screenings and breast cancer awareness, the Zonta ABC 5K/10K is dedicated to helping women afford preventative services who cannot afford them. This [...]
Race World Offshore Key West Championships
Key West Historic SeaportRace World Offshore is the premier offshore racing sanctioning body in the United States with some of the most experienced teams in all off offshore racing [...]
39th Annual 7-Mile Bridge Run
Key West Historic SeaportThe 7-Mile Bridge Run is put together by the Marathon Runners Club and is the only known run that is completely surrounded by water from [...]
36th Annual Schooner Wharf Bar Wrecker’s Race Cup
Schooner Wharf Bar 202 William St, Key West, FL, United StatesAhoy Mates! It's time to clean the bottom and pile on the sails in the 36th Annual Schooner Wharf Bar Wrecker's Race Cup!
37th Annual Schooner Wharf Wrecker’s Cup Race
Schooner Wharf Bar 202 William St, Key West, FL, United StatesAhoy Mates! It's time to clean the bottom and pile on the sails on March 27th No protests, no pageantry, just race with us - [...]
37th Annual Schooner Wharf Wrecker’s Cup Race
Schooner Wharf Bar 202 William St, Key West, FL, United States Ahoy Mates! It's time to clean the bottom and pile on the sails. This all-in-fun race series recalls the tradition of the wreckers in [...]
The Southernmost Regatta powered by Sailing Inc.
The Southernmost Regatta offers 5 consecutive days of high-quality racing on the picturesque blue waters of Key West, FL. The event is open to One [...]
2024 Annual Schooner Wharf Wreckers Cup Race – Second Race
Schooner Wharf Bar 202 William St, Key West, FL, United StatesAnnual Schooner Wharf Bar Wrecker’s Cup Race Series 2024 February 25 No protests, no pageantry, just race with us - or against us! Wrecker's Race [...]