A Positive Step of Monroe County

A Positive Step of Monroe County is an annual 5K run/walk held in Key West, Florida, with the 17th edition scheduled for December 13, 2025. The festive event encourages participants to wear holiday pajamas and starts and finishes at the Southernmost Beach Café on Duval Street. The scenic course passes notable landmarks including Casa Marina, Higgs Beach, and White Street Pier, with all miles clearly marked.

Open to runners and walkers of all ages and abilities, the race offers a fun atmosphere with refreshments, prizes, and a silent auction post-race. Proceeds support A Positive Step of Monroe County, a nonprofit aiding at-risk youth and families. Visit the organization's website for the most recent information.