PLACE:  2529 Cady Way, Winter Park, FL 32792

DESCRIPTION:  Holiday Five, December 27, 28, 29, 30, 31, 2026

What:               5 Distances and 5 days to choose from. 50K, Marathon, Half marathon, 10K, and 5K available 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 

Parking:            Cady Way Trailhead, near the Cady Way Pool. GPS coordinates: 

                          N 28.59458, W -081.31670

WAIT! Before you register, read everything below. Here are the main points:
     Races are not chip timed. We are old-fashioned hand timed. 
     Courses are not certified. No Boston qualifier. 
     No age group awards, no t-shirts, no useless bling.
     Cupless—bring your own bottle

These are low-key, casual, fun events. GREAT for first timers! These are not certified or sanctioned courses—meaning, NOT a Boston qualifier. Don’t expect much and maybe you won’t be disappointed. 

WHAT YOU DON’T GET: t-shirt, hat, socks, or any other apparel, great bling, cute reusable race bag, age group awards, spectators lining the course, large crowds cheering you in, hearty food at the finish, exciting music, and a party afterward.

WHAT YOU DO GET:  low entry fees, courses that are guaranteed not short, a simple finisher’s medal, a generous time limit, and a published finish time. But isn’t that all you really need? What do you do with all that other stuff anyway? You know you want to sign up. Really, where else can you run a marathon for $65?

COURSES:  The courses are NOT certified--no Boston qualifier here. The courses are lap courses, meaning that you will do an out-and-back multiple times. Which means you will see other runners going and coming. Not as boring as it might sound. In fact, many people come to prefer this course design. All the courses will be on primarily paved, urban run/bike trails that are fairly flat with some to a lot of shade. These are open courses and will be open to the public. This means there may be other runners, walkers and cyclists. 
 
-- The lap for the marathon, half marathon, and 50K is approximately 2.2 miles. The full marathon is twelve laps, the half is six laps, and the 50K is fourteen laps plus one short lap at the end. 

-- The lap for the 5K and 10K is approximately 1.55 miles—two laps for the 5K and four laps for the 10K. 

Turn-arounds for each distance will be clearly marked. We will have rubber bands to help you keep track of your laps.  

START / FINISH / AID STATION: The only aid station is at the start/finish location, which you will pass twice each lap. We will provide chilled water, Gatorade, soda, and sweet and salty snacks. 

CUPLESS: This is a cupless race. Meaning we would like for you to bring your own hydration device—water bottle, hydration belt/pack. There will be a table for your water bottles. We'll have small paper cups, but you'd be better off with your own bottle(s). 

HEAT:  Florida is typically hot and humid. We will provide ice for your water, Gatorade, and soda. There will also be a bucket of ice water for you to dip your hat, cooling towel, etc. We will have pickles and pickle juice, as well as a variety of salty snacks.  

BATHROOMS: The bathrooms are a little walk from the start/finish, but you’ll pass them during each lap. They're inside, permanent structure bathrooms with soap and water!

LIGHT: It will be just starting to break daylight at the start, but still dark in places on the course. (Sunrise is at 7:16.)  We recommend you have a light for the first half hour.

DROP BAG: There will be a location near the start/finish line where you may leave a drop bag.  

FINISH LINE: When you finish, ring the bell, or be sure to let the timer know you’re finished. Without this, you won’t get a finish time—or at least not an accurate time. Remember we are hand-timed—no timing chips! We won't know to record your time if you don't tell us you're done.

NOW, if you are STILL undecided (congratulations for reading this far), and you want to know what to expect, we won’t likely have world class athletes based on speed, but we will likely have world class athletes based on numbers of marathons completed. Think four-digit numbers. Just imagine the stories! These experienced runners love to meet new runners and offer encouragement and wisdom.

VOLUNTEERS: We always need volunteers. Each full volunteer day earns a free long run (half marathon or full marathon) or two short runs (5K or 10K).  Email at wingmanrunning@yahoo.com

Wingman Running Company