Run Key West

Race through Key West’s historic Old Town and waterfront areas January 17 & 18, 2026, during the 28^th Annual Key West Half Marathon. The field is quickly filling to capacity. We’ve added the Big Pecker Challenge which is the Half Marathon, 10K & 5K and the Lil’ Pecker Challenge which includes the 5K, 10K and 8K, along with a Papa’s Pilar Rum Stroll and Beach N’ Beer Mile Sunday afternoon!  Set to begin at 7am on Saturday with the 10K and 5K and 7am on Sunday with the Half Marathon & 8K.  All course’s run along the water and Sunday’s races run through Old Town Key West.  Run 1 or 2, 3 or all Four events!

Old Town Key West will host runners, fitness walkers and Beer Mile enthusiasts testing their skills and celebrating Ernest Hemingway’s sporting lifestyle on Saturday evening, July 26th. The longest on going race in Key West, the Hemingway 5K Sunset Run/Walk and Beach N’ Beer Mile was rated in 2018 #3 on Active.com’s list of top ten international destination races to turn into a vacation. Featured by Runner’s World as one of the Best 5Ks to Run this Summer.