Holiday Five 2026

The race.

Holiday Five takes place December 27–31, 2026, at the Cady Way Trail Head in Winter Park, FL. Five race distances are offered each day: 50K, marathon (26.2 miles), half marathon (13.1 miles), 10K (6.2 miles), and 5K (3.1 miles). The 50K, marathon, and half marathon start at 6:00 a.m., while the 10K and 5K start at 7:00 a.m., with a time limit of approximately 9.5 hours. The course is a paved, flat urban trail with two street crossings; longer races use loop formats on approximately 2.2-mile loops, while shorter races use 1.55-mile loops. Finishers receive a medal and access to water, Gatorade, sodas, and light snacks at the aid station. Participants must bring their own hydration device and should note that hand timing is used, requiring runners to notify staff when finished.