Holiday Five
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Holiday Five : Winter Park, FL, December 27–31, 2026
Holiday Five is a five-day running event held at Cady Way Trail Head, 2529 Cady Way, Winter Park, FL 32792. Each day offers one of five distance options so the same distances are available across the five successive days.
Distances offered:
- 50K - 31 Miles
- Marathon - 26.2 Miles
- Half marathon - 13.1 Miles
- 10K - 6.2 Miles
- 5K - 3.1 Miles
The start/finish and aid station are located at a small pavilion where runners may leave a drop bag. The paved urban run/bike trail is flat and partly shaded. The longer distances use a double out-and-back loop of approximately 2.2 miles; the marathon requires 12 loops, the half marathon 6 loops, and the 50K 14 loops plus two short "baby" loops. The 5K/10K course is approximately 1.55 miles with 2 and 4 loops respectively. Turnarounds will be clearly marked. This is an open course with two street crossings and trail users may be present.
Basic support at the pavilion includes water, Gatorade, sodas, and light sweet and salty snacks including pickles and pickle juice. Runners must bring their own hydration device; a table will be available for personal bottles and small cups will be provided for soda. Timing is hand-timed; finishers should ring the bell at the timing table and notify the timer to record an accurate time. The event lists an approximate time limit of 9.5 hours. Parking is at the Cady Way Trailhead near the Cady Way Pool, GPS N 28.59458, W -081.31670.
The event is described as low-key and minimal in amenities; there are no age-group awards, no elaborate giveaways, and limited post-race services. Volunteer service can earn a race entry credit per the organizer's policy. Visit the organization's website for the most recent information.
