Holiday Five
Holiday Five logo

Holiday Five

Winter Park, Florida, United States View on map
Dec 27, 2026 – Dec 31, 2026 (America/New_York local time)
Running

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

Dec 27, 2026 49.9K 6:00 AM
$350.00
Open

Holiday Five 50K, Day 1

Dec 27, 2026 49.9K 6:00 AM
$75.00
Open

Holiday Five Marathon, all five days

Dec 27, 2026 Marathon 6:00 AM
$300.00
Open

Holiday Five Marathon, Day 1

Dec 27, 2026 Marathon 6:00 AM
$65.00
Open

Holiday Five Half Marathon, all five days

Dec 27, 2026 Half-Marathon 6:00 AM
$250.00
Open

Holiday Five Half Marathon, Day 1

Dec 27, 2026 Half-Marathon 6:00 AM
$55.00
Open

Holiday Five 10K, all five days

Dec 27, 2026 10K 7:00 AM
$175.00
Open

Holiday Five 10K, Day 1

Dec 27, 2026 10K 7:00 AM
$40.00
Open

Holiday Five 5K, all five days

Dec 27, 2026 5K 7:00 AM
$125.00
Open

Holiday Five 5K, Day 1

Dec 27, 2026 5K 7:00 AM
$30.00
Open

Holiday Five 50K, Day 2

Dec 27, 2026 49.9K 6:00 AM
$75.00
Open

Holiday Five Marathon, Day 2

Dec 27, 2026 Marathon 6:00 AM
$65.00
Open

Holiday Five Half Marathon, Day 2

Dec 27, 2026 Half-Marathon 6:00 AM
$55.00
Open

Holiday Five 10K, Day 2

Dec 27, 2026 10K 7:00 AM
$40.00
Open

Holiday Five 5K, Day 2

Dec 27, 2026 5K 7:00 AM
$30.00
Open

Holiday Five 50K, Day 3

Dec 27, 2026 49.9K 6:00 AM
$75.00
Open

Holiday Five Marathon, Day 3

Dec 27, 2026 Marathon 6:00 AM
$65.00
Open

Holiday Five Half Marathon, Day 3

Dec 27, 2026 Half-Marathon 6:00 AM
$55.00
Open

Holiday Five 10K, Day 3

Dec 27, 2026 10K 7:00 AM
$40.00
Open

Holiday Five 5K, Day 3

Dec 27, 2026 5K 7:00 AM
$30.00
Open

Holiday Five 50K, Day 4

Dec 27, 2026 49.9K 6:00 AM
$75.00
Open

Holiday Five Marathon, Day 4

Dec 27, 2026 Marathon 6:00 AM
$65.00
Open

Holiday Five Half Marathon, Day 4

Dec 27, 2026 Half-Marathon 6:00 AM
$55.00
Open

Holiday Five 10K, Day 4

Dec 27, 2026 10K 7:00 AM
$40.00
Open

Holiday Five 5K, Day 4

Dec 27, 2026 5K 7:00 AM
$30.00
Open

Holiday Five 50K, Day 5

Dec 27, 2026 49.9K 6:00 AM
$75.00
Open

Holiday Five Marathon, Day 5

Dec 27, 2026 Marathon 6:00 AM
$65.00
Open

Holiday Five Half Marathon, Day 5

Dec 27, 2026 Half-Marathon 6:00 AM
$55.00
Open

Holiday Five 10K, Day 5

Dec 27, 2026 10K 7:00 AM
$40.00
Open

Holiday Five 5K, Day 5

Dec 27, 2026 5K 7:00 AM
$30.00
Open

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.

Temp (°C)
Minimum temperature (race-week average) 12.1° / Maximum temperature (race-week average) 20.9°
Feels Like (°C)
Minimum feels like — heat index / wind chill (race-week average) 11.2° / Maximum feels like — heat index / wind chill (race-week average) 20.9°
Peak wind (km/h)
Strongest wind of the day (race-week average)
14.4
Precip (mm)
Precipitation over the day (race-week average)
1.3mm
Humidity
Mean relative humidity (race-week average)
79.4%
Sunrise
Sunrise at the start line on December 27, 2026 (EST)
Sunset
Sunset at the start line on December 27, 2026 (EST)
Daylight
Hours between sunrise and sunset on race day
10h 20m

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

2025 edition View Results
2024 edition View Results
2023 edition View Results

Other races near Winter Park

Different organizers, within 40 miles, in the next three months

Find upcoming events by distance:

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

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