Holiday Five

DEC
27-31
2026
Five days of lap-based races in Winter Park offering 50K, marathon, half marathon, 10K and 5K on paved trails; hand timed and cupless.
27-31 Dec 2026
50 kilometers 26 miles 13 miles 6 miles 3 miles

Always double-check with the organizer's website! This page may contain affiliate links.

Holiday Five

Holiday Five runs December 27 to December 31, 2026 at Cady Way Trail Head, 2529 Cady Way, Winter Park, FL 32792. The event offers five distances each day on a lap course along primarily paved urban run and bike trails with shade. The courses are open to the public and may include other runners, walkers, and cyclists.

Distances offered:

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

The marathon, half marathon, and 50K use an approximate 2.2 mile lap. The marathon is twelve laps, the half marathon six laps, and the 50K fourteen laps plus one short lap. The 5K and 10K use an approximate 1.55 mile lap, two laps for the 5K and four laps for the 10K. Turnarounds will be clearly marked and rubber bands will be available to track laps.

The event is hand timed and not chip timed. Courses are not certified and are not Boston qualifying. The time limit is 9.5 hours. The only aid station is at the start/finish and will be passed twice each lap; chilled water, Gatorade, soda, ice, and sweet and salty snacks will be provided. The event is cupless; participants are expected to use their own hydration devices. Permanent bathrooms with soap and water are available and are passed on each lap. A drop bag location will be provided near the start/finish. Runners should expect limited amenities and a simple finisher recognition. Visit the organization's website for the most recent information.

50 km
Holiday Five 50k
26 mi
Holiday Five Marathon
13 mi
Holiday Five Half Marathon
6 mi
Holiday Five 10k
3 mi
Holiday Five 5k
Add Event
Help us complete the calendar!
  • Distance is at least 5 km
  • Event has a website or Facebook page
Website
Optional: Please provide your e-mail address if we may contact you.
Report a change
We will only update the data if the information is also on the website.