WRC Logo
runsignup.com

Holiday Five

location_city Winter Park

location_on Florida

flag United States

calendar_today 27 Dec, 2025 – 31 Dec, 2025

directions_run Running

language Official Website

Register

About the Event

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 and Marathon—6:00 am; Half Marathon—6:10 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 aware that these are low-key, bare bones, casual events. Set your expectations low—very low—so that your disappointment will be minimal. What we don’t provide we make up for in easy logistics and friendliness. 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 simple finisher’s medal, basic support (see below), and a VERY generous time limit. 

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 olives.

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 courses 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.

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 or 6:10, 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

Races Offered

Other

Dec 27, 2025

straighten

Distance — Other

terrain

Type — Road running

timer

Event has passed

5K

Dec 27, 2025

straighten

Distance — 5K

terrain

Type — Road running

timer

Event has passed

10K

Dec 27, 2025

straighten

Distance — 10K

terrain

Type — Road running

timer

Event has passed

Half-Marathon

Dec 27, 2025

straighten

Distance — Half-Marathon

terrain

Type — Road running

timer

Event has passed

Marathon

Dec 27, 2025

straighten

Distance — Marathon

terrain

Type — Road running

timer

Event has passed

Weather Overview

These values represent the 3-year monthly averages for December in Winter Park.

Temp (°C)
Feels Like (°C)
thermostat 13.0° / 21.5°
wb_sunny 11.4° / 20.6°
Wind (km/h)
Humidity (%)
air 11.7 /
water_drop 78.9%

About Winter Park

Scenic view of

Winter Park is a city of 31,000 people (2019) in Florida near Orlando. Winter Park is often seen as a popular tourist destination for those visiting Orlando that want an escape from the typical tourist scene of the Orlando theme parks. There is a quaint, local feel to the suburb even though there are a lot of tourists, especially during the winter months and holidays.

Read more launch

Hotels & Places to Stay

Nearby Races

2026 GYC 5K

2026 GYC 5K

location_on Orlando, Florida, US

calendar_today Jan 04, 2026

Recommended for You

Hand-picked events we think you’ll love.

Our pick
Run Manatee - Rye Preserve 5K -2026

Nov 21, 2026

Run Manatee - Rye Preserve 5K -2026

The RUN Manatee 5k series offers THREE adventures to celebrate ONE community. Participants will discover Manatee County…

Read more
Our pick
Turkey Trails - Sioux Falls

Nov 28, 2026

Turkey Trails - Sioux Falls

Join us for the annual Turkey Trails 5k/10k!  A fun, Thanksgiving-themed event that is perfect for the whole family.The…

Read more
Our pick
Candy Cane Course- Lincoln

Dec 13, 2026

Candy Cane Course- Lincoln

Join us for the annual Candy Cane Course 5k/12k!  A fun, Christmas-themed event that is perfect for the whole family.Th…

Read more
Our pick
Space Coast Triathlon and Duathlon

Mar 21, 2027

Space Coast Triathlon and Duathlon

WE ARE NOW OFFERING AN AQUABIKE DIVISION! Triathlon Information:Join us for the annual Space Coast Triathlon, held in …

Read more

Get race deals & updates

Subscribe to our newsletter for curated race picks and discounts.