Holiday Five

Holiday Five starts from the Cady Way Trail Head in Winter Park, Florida, on December 27, 2026. Five distances are on the program: the 50K (31 miles), the marathon (26.2 miles) and the half marathon (13.1 miles) at 6:00 a.m., then the 10K and the 5K at 7:00. The route is an urban trail, flat and partly shaded. Amenities stay basic — an aid station at the start and finish with light refreshments, runners carrying their own hydration, no age-group awards, a generous cutoff and a low entry fee.

Everything about the setup favors the runner who wants the distance rather than the production: flat trail, long time limit, cheap entry. That makes it a sensible place for a first marathon or a first 50K, provided you have rehearsed carrying your own fluids, since there is no on-course support to fall back on. For the marathon, a 16-week build with a weekly long run reaching 18 to 20 miles is the usual preparation; step up to 31 miles only once that long run is routine.