What should I bring for hydration?

The event is cupless, so you must bring your own hydration device such as a water bottle, belt, or pack.

How is the race timed?

The races are hand-timed; you must ring the bell at the timing table and notify the timer when you finish to ensure your time is recorded.

Do I need a headlamp?

If you are participating in the 50K, marathon, or half marathon starting at 6:00 am, you will need a light for the first half hour.

Are there age group awards or post-race parties?

No, these are low-key events that do not provide age group awards, music, parties, or hearty post-race food.

All races

11 weeks out

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All races

11 weeks out

Holiday Five

Sunday, December 27, 2026Winter Park, FL5K – 50K

The Holiday Five is a unique, five-day running event series held in Winter Park, Florida, offering distances ranging from 5K to 50K each day. These low-key, bare-bones events prioritize simplicity and friendliness over fanfare, making them perfect for runners who prefer a casual atmosphere. The course utilizes the paved, flat, and partially shaded Cady Way Trail, featuring a multi-loop format that ensures easy access to your vehicle and the aid station. Because the trail remains open to the public, participants should be prepared to share the path with local residents and navigate two street crossings safely. With a very generous time limit and a supportive community, this series is designed for those who value a straightforward, no-frills running experience. Please note that these events are hand-timed and cupless, so runners are encouraged to bring their own hydration gear.