Labor Day Triple

SEP
5-7
2026
Three consecutive days of looped trail races in Winter Park offering 50K, marathon, half marathon, 10K and 5K with hand timing and minimal race services.
5-7 Sep 2026
50 kilometers 26 miles 13 miles 6 miles 3 miles

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Labor Day Triple

The Labor Day Triple is a three day set of looped trail races held September 5 to September 7, 2026 at Cady Way Park trailhead, 2529 Cady Way, Winter Park, FL 32792.

Distances offered each day include:

  • 50K : 31 miles each day
  • Marathon : 26.2 miles each day
  • Half marathon : 13.1 miles each day
  • 10K : 6.2 miles each day
  • 5K : 3.1 miles each day

Each distance is run on a paved urban run and bike trail arranged as out and back laps. The marathon and half marathon lap is about 2.2 miles; the full marathon is twelve laps and the half is six laps. The 5K and 10K lap is about 1.55 miles with two laps for the 5K and four for the 10K. The 50K consists of fourteen marathon laps plus two small finishing laps. Turnarounds are clearly marked and rubber bands are provided for lap counting.

The event is hand timed and not chip timed. Courses are not certified and are not Boston qualifying. The format is no frills: no age group awards, no event apparel, and cupless aid at the loop start/finish so participants must bring their own hydration device. The aid station provides water, Gatorade, soda, salty and sweet snacks, and ice. A generous time limit is in place and lights are required for the longer distances during the early hours. Finishers should notify the timer to ensure an accurate recorded time. Volunteer shifts earn complimentary entries according to the event policy. Visit the organization's website for the most recent information.

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