HalfRuns
Holiday Five

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

Low KeyBare BonesEasy Parking

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

Directions

Course Info

Course Type

Loop Course

Terrain

road

Difficulty

Ultra-Flat

Net Drop/km

0 m (Flat)

Separation

0.0%

Also Offers

31 Miles26.2 Miles13.1 Miles6.2 Miles3.1 Miles

Quality Score

Methodology
Heritage6/20

3 years running

Size6/15

~16 finishers a year

Momentum3/5

small race — neutral

Loyalty0/20

13% returning runners

Course & details3/15

4 timing sources

National draw5/10

runners from 6 states

Front-pack speed0/5

winner 1:42:48

Weather5/10

typical high 70°F

Race Day Weather

5-year historical avg

Start (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

10%
25%
75%
90%
1:20p50 median ≈ 3:106:50

Turnout by year

2023–2025

'23'24'25
See full results

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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