Holiday Five

About the race

Holiday Five takes place December 27–31, 2026 at the Cady Way Trail Head, 2529 Cady Way, Winter Park, FL 32792 (near the Cady Way Pool; GPS N 28.59458, W -081.31670). The event runs five consecutive days with racing options available each day.

Distances offered:

• 50K (listed as 31 Miles)
• Marathon (26.2 Miles)
• Half marathon (13.1 Miles)
• 10K (6.2 Miles)
• 5K (3.1 Miles)

Racing options include single-day entries and multi-day entries that cover all five days for each distance. The 50K, marathon, and half marathon use an out-and-back loop of approximately 2.2 miles: marathon 12 loops, half marathon 6 loops, 50K 14 loops plus one small lap. The 5K and 10K use an approximately 1.55-mile loop: 2 and 4 loops respectively. Turnarounds are clearly marked. The course is a paved, urban run/bike trail that is flat, partly shaded, and on an open course with two street crossings; runners must cross streets safely and share the trail with local users.

Support is basic. The start/finish and aid station are close to the bathrooms and the aid station is passed twice each lap. Available items include water, Gatorade, sodas, and light sweet and salty snacks, including pickles and pickle juice. The event is cup-less for the most part; runners should bring their own hydration device. There is convenient parking at the trailhead and cars can be passed during laps. Timing is hand timed; finishers should ring the bell at the timing table and notify the timer for an accurate time. The overall time limit is approximately 9.5 hours.

The organizer describes the event as low-key and bare bones. The event does not include age-group awards, specialty shirts or hats, extensive finisher swag, large crowds or post-race parties, or plentiful finish-line food. It does provide low entry fees, a finisher’s medal, basic aid support, and friendly on-site staff and fellow runners. Visit the organization's website for the most recent information.

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