

Holiday Five
Race Date
Dec 27, 2026
Location
Winter Park, FL
Quick facts
- Date
- Sunday, December 27, 2026
- Location
- Winter Park, Florida
- Distance
- Half marathon (13.1 mi) + 31 Miles, 26.2 Miles, 13.1 Miles, 6.2 Miles, 3.1 Miles
- Course
- Loop Course
- Terrain
- Road
- USATF certified
- Not listed
- Finishers on record
- 153
Highlights
Atmosphere
The Experience
PLACE: 2529 Cady Way, Winter Park, FL 32792 DESCRIPTION: Holiday Five, December 27, 28, 29, 30, 31, 2026 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 near the aid station a short distance from the bathrooms. The aid station 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 an out-and-back course of approximately 2.2 miles; marathon 12 loops, half marathon 6 loops, 50K 14 loops plus 1 small lap. 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. Cup-less: 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 wingmanrunning@yahoo.com Wingman Running Company
Logistics
Race Day
Sunday, December 27, 2026
Start Time
6:00 AM
Start Location
Cady Way Trail Head, Winter Park, FL, 32792
Course Info
Course Type
Loop Course
Terrain
road
Difficulty
Ultra-Flat
Net Drop/km
0 m (Flat)
Separation
0.0%
Also Offers
Quality Score
3 years running
~16 finishers a year
small race — neutral
13% returning runners
4 timing sources
runners from 6 states
winner 1:42:48
typical high 70°F
Race Day Weather
5-year historical avgStart (Low)
54°
Afternoon (High)
70°
Pleasant conditions — light layers at start, comfortable by finish
0.0"
Precipitation
9 mph
Wind
79%
Humidity
Historical Finish Times
How 153 finishers actually crossed the line across 3 years.
Most recent
2025
Total finishers
153
Median time
~3:10
Latest turnout
—
States
24
Turnout by year
2023–2025
Hover the histogram to inspect specific finish times.
Race Photos
Frequently asked
When is the Holiday Five?
The Holiday Five is held on Sunday, December 27, 2026, starting at 6:00 AM.
Where does the Holiday Five take place?
It takes place in Winter Park, Florida.
What distances does the Holiday Five offer?
The half marathon (13.1 miles), plus 31 Miles, 26.2 Miles, 13.1 Miles, 6.2 Miles, 3.1 Miles.
Is the Holiday Five course flat and good for a PR?
The Holiday Five is a ultra-flat, loop course course.
How many people run the Holiday Five?
HalfRuns has finish records for 153 runners who have completed the Holiday Five.
HalfRuns editorial — independent, no paid placement.
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