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
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. 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, 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 cheap 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, Coke, Diet Mountain Dew, 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 marathon/half marathon course is twelve and six out-and-back loops of approximately 2.2 miles, respectively. The 5K and 10K courses are two and four laps of approximately 1.55 miles. Turn arounds will be clearly marked. The trail is popular with local residents, so be prepared to share.
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 cups for the soda.)
Light: If you start at 6:00 or 6:10, you will need a light for the first hour.
