Holiday Five
About this race
PLACE: 2529 Cady Way, Winter Park, FL 32792
DESCRIPTION: Holiday Five, December 27, 28, 29, 30, 31, 2025
What: 5 Distances, 5 days. 50K, Marathon, Half marathon, 10K, and 5K each day.
Where: Cady Way Trail Head, 2529 Cady Way, Winter Park, FL 32792
Start Times: 50K, Marathon, and Half marathon—6:00 am; 5K and 10K—7:00 am.
Time limit: 9.5 hours (or so)
Parking: Cady Way Trailhead, near the Cady Way Pool. GPS coordinates:
N 28.59458, W -081.31670
WARNING: Before you continue, be warned that these are low-key, bare bones, casual events. Set your expectations low—very low—so that your disappointment will be minimal. But wait! We have easy logistics, great course, and an abundance of friendliness. Also, very convenient parking—pass your car every lap. If you’re still interested, here’s what to expect.
You WILL NOT get age group awards, a cleverly designed t-shirt or hat, great bling (actually, any bling), cute reusable race bag filled with goodies, spectators lining the course, crowds cheering you in, hearty food at the finish, exciting music, or a party afterward.
You WILL get low entry fees, courses that are guaranteed not short, a nice finisher’s medal, basic support (see below), a VERY generous time limit, and lots of friendly support from staff and runners. Also, convenient locations for supporters.
Start/Finish and Aid Station: The start and finish are in a small pavilion, where you may leave a drop bag. This is also the aid station, which you will pass twice each lap. (More about laps below.) We will provide water, Gatorade, sodas, and light sweet and salty snacks, including pickles and pickle juice.
Courses: The paved, urban run/bike trail is flat and partly shaded. This is an open course, and includes two street crossings. You are responsible for crossing safely. The 50K/marathon/half marathon course is a double out-and-back loop of approximately 2.2 miles; marathon 12 loops, half marathon 6 loops, 50K 14 loops plus 2 "baby" loops. The 5K/10K course is approximately 1.55 miles, 2 and 4 loops respectively. Turn arounds will be clearly marked. The trail is popular with local residents, so be prepared to share. For more information about the courses, see Detailed Course Description above.
Finish: When you are finished, ring the bell at the timing table and let the timer know you're finished. That's the only way to get an accurate time. Remember we are hand-timed. If you don't tell us, we won't know.
Cupless: Bring your own hydration device—water bottle, hydration belt/pack. There will be a table at the start/finish for your bottles. (We will have small cups for the soda.)
Light: If you start at 6:00, you will need a light for the first half hour.
Volunteers Needed: Each volunteer day earns a free race entry for yourself or someone else for either one long race (50K, marathon, or half marathon) or for two short races (5K or 10K). Contact Bettie at bettiemw@gmail.com.
BMW Running Company
Pick your distance
Running
Holiday Five 50K, all five days
Holiday Five 50K, Day 1
Holiday Five Marathon, all five days
Holiday Five Marathon, Day 1
Holiday Five Half Marathon, all five days
Holiday Five Half Marathon, Day 1
Holiday Five 10K, all five days
Holiday Five 10K, Day 1
Holiday Five 5K, all five days
Holiday Five 5K, Day 1
Holiday Five 50K, Day 2
Holiday Five Marathon, Day 2
Holiday Five Half Marathon, Day 2
Holiday Five 10K, Day 2
Holiday Five 5K, Day 2
Holiday Five 50K, Day 3
Holiday Five Marathon, Day 3
Holiday Five Half Marathon, Day 3
Holiday Five 10K, Day 3
Holiday Five 5K, Day 3
Holiday Five 50K, Day 4
Holiday Five Marathon, Day 4
Holiday Five Half Marathon, Day 4
Holiday Five 10K, Day 4
Holiday Five 5K, Day 4
Holiday Five 50K, Day 5
Holiday Five Marathon, Day 5
Holiday Five Half Marathon, Day 5
Holiday Five 10K, Day 5
Holiday Five 5K, Day 5
Typical race-day weather
Based on 4 years of Open-Meteo archive data for this event's race dates in Winter Park, plus the 3 days either side.
The sun rises at 7:16 AM and sets at 5:36 PM local time (EST) in Winter Park on December 27, 2026 — 10h 20m of daylight.
Course
No course map published yet.
The organizer hasn't released a route for this event, and we don't publish guesses. If you're the organizer, send us a GPX file and we'll draw the profile.
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Results — Holiday Five
Other races near Winter Park
Different organizers, within 40 miles, in the next three months
Stuff Your Face Race
Heartbeat for Jesus 5k
Inaugural race - May
Jingle Bell Run - Orlando, FL
🏃 Plan Your Next Race in Winter Park
Find upcoming events by distance:
- Winter Park 5K Races 7 races
- 10K Run Events in Winter Park 6 races
- Winter Park Half Marathons 6 races
- Marathons in Winter Park 6 races
- Winter Park Running Calendar 2026 7 races
Where this page comes from. Race details were last updated on . We re-check listings regularly and again in the week before race day.
- Entries, prices, waves and inclusions — the event's official registration page
- Temperature and humidity — Copernicus ERA5 reanalysis via Open-Meteo (CC BY 4.0)
- Elevation and terrain relief — Copernicus DEM GLO-90, ESA (CC BY 4.0)
- Comparisons and counts — Race Discovery calendar, 7 Winter Park events
Spotted something wrong? Tell us and we'll fix it.