About This Race

Course & Race Day Details

T-Shirt & Medal
Race Swag
Papa’s Pilar Rum Stroll, Key West Half Marathon, Key West 5K, Big Pecker Run Anywhere, Lil Pecker Run Anywhere, Lil' Pecker Challenge (5K, 8K AND 10K) THREE MEDALS AND A LIL' PECKER HAT!, Key West 10K, Key West Beach N' Beer Mile: T-Shirt | BIG PECKER CHALLENGE- (Half Marathon, 10K and 5K) FOUR MEDALS! Special Medal for the Big Pecker!, Run Anywhere 10K, Key West 8K, Run Anywhere 1/2 Marathon, Run Anywhere 5K, Run Anywhere 8K: T-Shirt & Medal

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Choose Your Distance

Papa’s Pilar Rum Stroll
Hemingway Rum Stroll Presented by Papa’s Pilar Rum includes six locations with a Papa’s Pilar Rum drink at each location. Must be over 21, Entry Fee: $75 includes Custom Rum Stroll Race Shirt. More details to Come!
$75.00
Increases Jan 16
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BIG PECKER CHALLENGE- (Half Marathon, 10K and 5K) FOUR MEDALS! Special Medal for the Big Pecker! Half Marathon
1/17/26 - 7:00 am: 5K Start and Finish Location: Higg’s Beach on 1000 Atlantic Blvd. 1/17/26 - 8:00 am: 10K Start and Finish Location: Higg’s Beach on 1000 Atlantic Blvd. 1/18/26- 7:00 am: Half Marathon Location: corner of Caroline Street & Trumbo Road/West Marine (less than two blocks from the Packet Pick-Up location.)
$278.95
Increases Jun 30
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Key West Half Marathon Half Marathon
The half marathon course has you run past some of the most iconic places in Key West! You'll run up Duval Street, past the Southernmost Point and along beautiful Smathers Beach. The finish line is right by the Half Shell Raw Bar and there will be plenty of refreshments waiting for you there!
$145.95
Increases Jun 30
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Key West 5K 5K
The 5K course has you starting by Higg's Beach and the beautiful waterfront of Smather's Beach.
$65.95
Increases Jun 30
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Tour Of Key West (Virtual Tour)
This is not a competitive event! Chose this event if you want a nice tour of Key West. It will take you around some of the cool spots on the island. There are plenty of stores along the way to grab a drink or snack as you go. The idea is to have fun and be safe.
TBD
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Run Anywhere 10K 10K
$72.95
Increases Jun 30
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Big Pecker Run Anywhere
$260.95
Increases Jun 30
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Lil Pecker Run Anywhere
$200.00
Increases Jun 30
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Lil' Pecker Challenge (5K, 8K AND 10K) THREE MEDALS AND A LIL' PECKER HAT! 5K
1/17/26 - 7:00 am: 5K Start and Finish Location: Higg’s Beach on 1000 Atlantic Blvd. 1/17/26 - 8:00 am: 10K Start and Finish Location: Higg’s Beach on 1000 Atlantic Blvd. 1/18/26- 7:30 am: 8K Location: corner of Caroline Street & Trumbo Road/West Marine (less than two blocks from the Packet Pick-Up location.)
$208.00
Increases Jun 30
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Key West 8K 8K
$70.95
Increases Jun 30
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Key West 10K 10K
$76.95
Increases Jun 30
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Key West Beach N' Beer Mile
Key West Beach N’ Beer Mile – 3:00 pm 4 Loops, 4 Beers, Custom Shirt and Raffles! Race is NOT TIMED! Prizes awarded for Best Team Spirit, Best Dressed, Least Dressed Raffles at 5 pm sharp.
$49.00
Increases Jun 30
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Run Anywhere 1/2 Marathon Half Marathon
This is the virtual half marathon. Run where you want and submit your results between January 16th and 20th!
$124.95
Increases Jun 30
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Run Anywhere 5K 5K
This is the virtual 5k. Run where you want and submit your results between January 16th and 20th!
$65.95
Increases Jun 30
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Run Anywhere 8K 8K
$67.95
Increases Jun 30
Register