Run Key West

Race through Key West’s historic Old Town and scenic waterfront on January 16–17, 2027, during the 29th Annual Key West Half Marathon. Registration is filling quickly.

This year features two multi-race challenges:

• Big Pecker Challenge: Half Marathon + 10K + 5K

• Lil’ Pecker Challenge: 5K + 10K + 8K

The weekend also includes the Papa’s Pilar Rum Stroll and the Beach N’ Beer Mile on Sunday afternoon.

Race Schedule
Saturday:

• 5K – 7:00 AM

• 10K – 8:00 AM

Sunday:

• Half Marathon – 7:00 AM

• 8K – 7:30 AM

All courses run along the water, with Sunday’s races winding through the streets of Old Town Key West.

Run one race, two races, three races—or all four events and make it a full race weekend in Key West. 🏃‍♂️🌴

Old Town Key West will welcome runners, fitness walkers, and Beer Mile enthusiasts on Saturday evening, July 24, 2027, for an event celebrating Ernest Hemingway’s sporting lifestyle. The Hemingway 5K Sunset Run/Walk begins at 7:30 PM, offering participants a scenic evening run through historic Key West.

The Hemingway 5K Sunset Run/Walk is the longest-running race in Key West. In 2018, it was ranked #3 on Active.com’s list of the Top 10 International Destination Races to Turn into a Vacation and was also featured by Runner’s World as one of the Best 5Ks to Run This Summer.

The weekend also includes the Beach N’ Beer Mile, set for Sunday, July 25, 2027 at noon, where participants test their speed and endurance in this spirited challenge.

These popular athletic events are part of Hemingway Days, a six-day celebration honoring the life and work of the legendary author who lived and wrote in Key West throughout much of the 1930s. 🍻🏃‍♂️🌅