Holiday Five 2026

Holiday Five is a small race series in Winter Park, starting at 6:00 AM EST, offering 50K, marathon, half marathon, 10K, and 5K distances. The field is typically small, ranging from 1 to 100 participants, giving it the feel of a low-key local event rather than a large production. The races take place on a paved, partly shaded bike path within an urban environment. The course is fast and flat, with average temperatures between 53 and 72 degrees. Easy parking and a generous time limit make it accessible for first-time participants, casual runners, and those seeking a straightforward race experience.