Holiday Five

Experience the ultimate running adventure at Holiday Five, a unique event happening in Winter Park, Florida from December 27th to December 31st, 2025. Participants can conquer five different distances in five days – 50K, Marathon, Half Marathon, 10K, and 5K – all starting at the Cady Way Trail Head. The course offers a flat, shaded route through picturesque trails, catering to runners of all levels in a friendly atmosphere. Featuring ample time limits and essential support at the aid station, Holiday Five prioritizes camaraderie over competition. While there are no age group awards or flashy medals, the event boasts affordable fees, seamless organization, and the pure satisfaction of achieving your chosen distance. Kick off the New Year with a rewarding and enjoyable running experience in stunning Winter Park!