Holiday Five (Five Days, Five Distances to choose from)
- Date Sun 27th December 2026 - Thu 31st December 2026
- Time 6:00AM EST
- Location Winter Park, Florida
- Price $32.80 - $368.50
- Races 30 races
- Distances Ultra, Marathon, Half Marathon, 10km, 5km
Event summary
Whether you're a seasoned marathoner or a first-time runner, the Holiday Five promises a laid-back, community-focused atmosphere. With low entry fees and a generous time limit, you can enjoy the beauty of the urban trails while meeting fellow enthusiasts along the lap courses. Experience the thrill of running in a friendly, non-competitive environment—where the emphasis is on fun rather than formalities. Plus, this cupless event encourages sustainability by asking participants to bring their own hydration devices. Join us for an unforgettable holiday running experience in the heart of Winter Park!
Organiser's Description
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 marathon6:00 am; 5K and 10K7:00 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.
Cuplessbring your own bottle
These are low-key, casual, fun events. GREAT for first timers! These ARE NOT CERTIFIED OR SANCTIONED COURSESmeaning, NOT a Boston qualifier. Dont expect much and maybe you wont be disappointed.
WHAT YOU DONT 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 finishers medal, a generous time limit, and a published finish time. But isnt 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 milestwo 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 devicewater 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 youll 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 youre finished. Without this, you wont get a finish timeor at least not an accurate time. Remember we are hand-timedno 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 wont 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
Races
-
Holiday Five 50K, All Five Days
Incl. $18.50 Fee
Sun 27th December 2026 (6:00AM EST)
$368.50
-
Holiday Five 50K, Day 1
Incl. $5.50 Fee
Sun 27th December 2026 (6:00AM EST)
$80.50
-
Holiday Five 50K, Day 2
Incl. $5.50 Fee
Mon 28th December 2026 (6:00AM EST)
$80.50
-
Holiday Five 50K, Day 3
Incl. $5.50 Fee
Tue 29th December 2026 (6:00AM EST)
$80.50
-
Holiday Five 50K, Day 4
Incl. $5.50 Fee
Wed 30th December 2026 (6:00AM EST)
$80.50
-
Holiday Five 50K, Day 5
Incl. $5.50 Fee
Thu 31st December 2026 (6:00AM EST)
$80.50
-
Holiday Five Marathon, All Five Days
Incl. $16.00 Fee
Sun 27th December 2026 (6:00AM EST)
$316.00
-
Holiday Five Marathon, Day 1
Incl. $4.90 Fee
Sun 27th December 2026 (6:00AM EST)
$69.90
-
Holiday Five Marathon, Day 2
Incl. $4.90 Fee
Mon 28th December 2026 (6:00AM EST)
$69.90
-
Holiday Five Marathon, Day 3
Incl. $4.90 Fee
Tue 29th December 2026 (6:00AM EST)
$69.90
-
Holiday Five Marathon, Day 4
Incl. $4.90 Fee
Wed 30th December 2026 (6:00AM EST)
$69.90
-
Holiday Five Marathon, Day 5
Incl. $4.90 Fee
Thu 31st December 2026 (6:00AM EST)
$69.90
-
Holiday Five Half Marathon, All Five Days
Incl. $13.50 Fee
Sun 27th December 2026 (6:00AM EST)
$263.50
-
Holiday Five Half Marathon, Day 1
Incl. $4.30 Fee
Sun 27th December 2026 (6:00AM EST)
$59.30
-
Holiday Five Half Marathon, Day 2
Incl. $4.30 Fee
Mon 28th December 2026 (6:00AM EST)
$59.30
-
Holiday Five Half Marathon, Day 3
Incl. $4.30 Fee
Tue 29th December 2026 (6:00AM EST)
$59.30
-
Holiday Five Half Marathon, Day 4
Incl. $4.30 Fee
Wed 30th December 2026 (6:00AM EST)
$59.30
-
Holiday Five Half Marathon, Day 5
Incl. $4.30 Fee
Thu 31st December 2026 (6:00AM EST)
$59.30
-
Holiday Five 10K, All Five Days
Incl. $11.50 Fee
Sun 27th December 2026 (7:00AM EST)
$186.50
-
Holiday Five 10K, Day 1
Incl. $3.40 Fee
Sun 27th December 2026 (7:00AM EST)
$43.40
-
Holiday Five 10K, Day 2
Incl. $3.40 Fee
Mon 28th December 2026 (7:00AM EST)
$43.40
-
Holiday Five 10K, Day 3
Incl. $3.40 Fee
Tue 29th December 2026 (7:00AM EST)
$43.40
-
Holiday Five 10K, Day 4
Incl. $3.40 Fee
Wed 30th December 2026 (7:00AM EST)
$43.40
-
Holiday Five 10K, Day 5
Incl. $3.40 Fee
Thu 31st December 2026 (7:00AM EST)
$43.40
-
Holiday Five 5K, All Five Days
Incl. $8.50 Fee
Sun 27th December 2026 (7:00AM EST)
$133.50
-
Holiday Five 5K, Day 1
Incl. $2.80 Fee
Sun 27th December 2026 (7:00AM EST)
$32.80
-
Holiday Five 5K, Day 2
Incl. $2.80 Fee
Mon 28th December 2026 (7:00AM EST)
$32.80
-
Holiday Five 5K, Day 3
Incl. $2.80 Fee
Tue 29th December 2026 (7:00AM EST)
$32.80
-
Holiday Five 5K, Day 4
Incl. $2.80 Fee
Wed 30th December 2026 (7:00AM EST)
$32.80
-
Holiday Five 5K, Day 5
Incl. $2.80 Fee
Thu 31st December 2026 (7:00AM EST)
$32.80
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Cady Way Trail Head, 2529 Cady Way, Winter Park, 32792, FL, United States
Holiday Five (Five Days, Five Distances to choose from)
