Labor Day Triple

SEP
5-7
2026
Experience a low key multi day running event in Winter Park featuring distances from 5K to 50K. Run one day or take on the triple challenge over Labor Day weekend on a flat and shaded paved trail.
5-7 Sep 2026
31 miles 26 miles 13 miles 6 miles 3 miles

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Labor Day Triple

The Labor Day Triple is a multi-day running event held at Cady Way Park in Winter Park, Florida. The event takes place over three consecutive days during Labor Day weekend, offering participants the opportunity to compete in several distances each day. The available distances include:

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

Participants can choose to run a single day or register for all three days. The races are held on a paved urban run/bike trail. The course is a lap-based design featuring a double out-and-back format. For the marathon and half marathon, each lap is approximately 2.2 miles, with the full marathon consisting of twelve laps and the half marathon six. The 5K and 10K use a 1.55-mile lap, requiring two and four laps respectively. The 50K involves fourteen of the longer laps plus two smaller additional loops.

The event is hand-timed rather than chip-timed, and courses are not certified. The terrain is flat and largely shaded, though it remains an open course with two street crossings per lap. This is a cupless event, requiring runners to bring their own hydration devices. An aid station at the start/finish area provides water, electrolyte drinks, soda, and various sweet and salty snacks. Due to the early start, participants in the 50K, marathon, and half marathon are required to use a light for the initial hours.

Amenities include a simple finisher's medal and a nine-hour time limit. A pavilion is available at the start/finish area for drop bags, and public bathrooms are located a short walk from the course loop. Visit the organization's website for the most recent information.

31 mi
50k
26 mi
Marathon
13 mi
Half Marathon
6 mi
10k
3 mi
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