Holiday Five
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Event details
Holiday Five runs from December 27 to December 31, 2025 in Winter Park, Florida. The venue is Cady Way Trail Head, 2529 Cady Way, Winter Park, FL 32792. The event offers the following distances each day:
- 50K
- Marathon
- Half marathon
- 10K
- 5K
A time limit of approximately 9.5 hours applies for the long-distance events. Parking is at the Cady Way Trailhead near the Cady Way Pool. GPS coordinates are N 28.59458, W -081.31670. Registration price ranges are listed by distance.
Course and logistics
Courses use a paved, urban run and bike trail that is flat and partly shaded. The long-course layout is a double out-and-back loop of about 2.2 miles; the marathon is 12 loops, the half marathon is 6 loops, and the 50K is 14 loops plus two short "baby" loops. The 5K/10K course is about 1.55 miles with 2 and 4 loops respectively. Turnarounds are clearly marked. The course is open to the public and includes two street crossings; participants are responsible for crossing safely.
The start/finish is at a small pavilion that serves as the aid station and drop-bag location. Aid is provided twice per lap and includes water, Gatorade, sodas, and light snacks such as pickles and olives. Timing is hand-timed; finishers should ring the bell at the timing table and notify the timer to record a time. The event is described as low-key with basic support and a simple finisher’s medal. Visit the organization's website for the most recent information.
