location_city Winter Park
location_on Florida
flag United States
calendar_today 27 Dec, 2025 – 31 Dec, 2025
directions_run Running
language Official Website
RegisterPLACE: 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
Dec 27, 2025
Distance — Other
Type — Road running
Event has passed
Dec 27, 2025
Distance — 5K
Type — Road running
Event has passed
Dec 27, 2025
Distance — 10K
Type — Road running
Event has passed
Dec 27, 2025
Distance — Half-Marathon
Type — Road running
Event has passed
Dec 27, 2025
Distance — Marathon
Type — Road running
Event has passed
These values represent the 3-year monthly averages for December in Winter Park.
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.
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