Holiday Five

Holiday Five is a five-day running event held December 27–31, 2025, at the Cady Way Trail Head in Winter Park, Florida. It features five daily distances—50K, marathon, half marathon, 10K, and 5K—across five days. The flat, paved urban trail is open and partly shaded, with two street crossings.

Courses use loops: the long distances run multiple laps (roughly 2.2 miles per lap; 12 marathon loops, 6 half-marathon loops, 14 50K loops plus two small loops), while 5K/10K are about 1.55 miles per loop. Start/finish is a small pavilion with a basic aid station and a cupless policy; finish times are hand-timed. The event emphasizes easy logistics, friendliness, ample time, simple finisher medals, and on-site parking. Visit the organization's website for the most recent information.