Holiday Five
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Holiday Five : Winter Park, FL
The Holiday Five is a multi-day running event held December 27–31, 2025 at Cady Way Trail Head, 2529 Cady Way, Winter Park, FL 32792 (GPS N 28.59458, W -081.31670). The event offers five distances each day:
- 50K
- Marathon
- Half marathon
- 10K
- 5K
Course and logistics
The courses run on a paved, urban run/bike trail that is flat and partly shaded. The course is open to the public and includes two street crossings; participants are responsible for crossing safely. The 50K/marathon/half courses use a double out-and-back loop of about 2.2 miles (marathon 12 loops, half marathon 6 loops, 50K 14 loops plus two short "baby" loops). The 5K/10K course is about 1.55 miles (2 and 4 loops respectively). Turnarounds are clearly marked.
Start and finish are at a small pavilion that also serves as the aid station and drop-bag area. The aid table provides water, Gatorade, sodas, and light sweet and salty snacks, including pickles and olives. The event is cupless; participants should bring their own hydration device. Timing is hand-timed; finishers must signal the timing table to record an accurate time. Parking is at the Cady Way Trailhead near the pool. Volunteers may earn free race entries per volunteer day. Visit the organization's website for the most recent information.