Holiday Five
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Holiday Five
Holiday Five is a series of runs held in Winter Park, Florida on December 27 through December 31, 2026. Events take place at the Cady Way Trail Head, 2529 Cady Way, Winter Park FL 32792, with parking near the Cady Way Pool (GPS N 28.59458, W -081.31670).
Distances offered each day include:
- 50K
- Marathon
- Half marathon
- 10K
- 5K
Courses run on a paved urban run and bike trail that is flat and partly shaded. The longer course uses 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 loops. The 5K and 10K use an approximately 1.55 mile loop run two or four times. The course is open to the public and includes two street crossings; runners are responsible for crossing safely.
Start and finish are at a small pavilion that also serves as the aid station and drop bag location. The aid table is passed twice each lap and will offer water, Gatorade, sodas, and light sweet and salty snacks including pickles and pickle juice. Participants should bring their own hydration device; a table is provided for personal bottles. There is a generous approximate time limit of 9.5 hours. Timing is by hand; to record a finish runners must ring the bell at the timing table and notify the timer.
This series is presented as low key and basic in support. There are no age group awards, no event t-shirt or hat, and no post race party. Volunteers earn a free race entry for one long race or two short races. Visit the organization's website for the most recent information.
