Holiday Five

DEC
27-31
2026
Experience a casual multi day running series in Winter Park featuring five distances from 5K to 50K. Enjoy a flat paved course with easy logistics and the flexibility to run a single day or the full five day challenge.
27-31 Dec 2026
31 miles 26 miles 13 miles 6 miles 3 miles

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Event Overview

Holiday Five is a multi-day running series held in Winter Park, Florida. The event takes place at the Cady Way Trail Head and offers five different distances each day over a five-day period. Participants can choose to run on individual days or commit to the same distance for all five days.

The available distances for the event include:

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

Course Details

The races are held on a paved, urban multi-use trail that is flat and partially shaded. This is an open course, meaning runners will share the path with local residents and must navigate two street crossings safely. The long-distance courses (50K, marathon, and half marathon) utilize a double out-and-back loop of approximately 2.2 miles. The 5K and 10K events use a 1.55-mile loop.

Logistics and Support

The event is organized as a low-key, casual race with basic support. A single aid station is located at a pavilion near the start and finish area, which participants pass multiple times during their laps. This station provides water, electrolyte drinks, soda, and light snacks.

This is a cupless event, and participants are required to bring their own hydration devices, such as water bottles or hydration packs. Timing is conducted manually; runners must ring a bell at the timing table upon completion to record their results. A time limit of approximately 9.5 hours is provided for participants. Parking is located at the Cady Way Trailhead near the Cady Way Pool, allowing runners to pass their vehicles during each lap. Visit the organization's website for the most recent information.

31 mi
Holiday Five 50k
26 mi
Holiday Five Marathon
13 mi
Holiday Five Half Marathon
6 mi
Holiday Five 10k
3 mi
Holiday Five 5k