Holiday Five
- Date Sat 27th December 2025 - Wed 31st December 2025
- Time 6:00AM EST
- Location Winter Park, Florida
- Price $32.80 - $368.50
- Races 30 races
- Distances Half Marathon, 10km, 5km, Ultra
Event summary
With early start times at 6:00 am for the 50K and Marathon, and 7:00 am for the 5K and 10K, you'll have plenty of time to enjoy the flat, paved, and partly shaded trail while soaking up the holiday spirit. The relaxed atmosphere promises a casual running experience with easy logistics, basic support, and a generous 9.5-hour time limit. While this event is all about simplicity—no frills, no age group awards, and no elaborate finishers' swag—you'll get to enjoy the camaraderie of fellow runners and the thrill of completing your chosen distance. Don’t miss this chance to kick off your New Year with a memorable running adventure!
Organiser's Description
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 Marathon6:00 am; Half Marathon6:10 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
WARNING: Before you continue, be warned that these are low-key, bare bones, casual events. Set your expectations lowvery lowso that your disappointment will be minimal. What we dont provide we make up for in easy logistics and friendliness. Convenient parkingpass your car every lap. If youre still interested, heres 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 finishers 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.
CUPLESS: Bring your own hydration devicewater 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.
VOLUNTEERS NEEDED: Each volunteer day earns a free race entry for yourself or someone else. Contact Bettie at [email protected].
Races
-
Holiday Five Marathon, All Five Days
Incl. $16.00 Fee
Sat 27th December 2025 (6:00AM EST)
$316.00
-
Holiday Five Marathon, Day 1
Incl. $4.90 Fee
Sat 27th December 2025 (6:00AM EST)
$69.90
-
Holiday Five Marathon, Day 2
Incl. $4.90 Fee
Sun 28th December 2025 (6:00AM EST)
$69.90
-
Holiday Five Marathon, Day 3
Incl. $4.90 Fee
Mon 29th December 2025 (6:00AM EST)
$69.90
-
Holiday Five Marathon, Day 4
Incl. $4.90 Fee
Tue 30th December 2025 (6:00AM EST)
$69.90
-
Holiday Five Marathon, Day 5
Incl. $4.90 Fee
Wed 31st December 2025 (6:00AM EST)
$69.90
-
Holiday Five Half Marathon, All Five Days
Incl. $13.50 Fee
Sat 27th December 2025 (6:10AM EST)
$263.50
-
Holiday Five Half Marathon, Day 1
Incl. $4.30 Fee
Sat 27th December 2025 (6:10AM EST)
$59.30
-
Holiday Five Half Marathon, Day 2
Incl. $4.30 Fee
Sun 28th December 2025 (6:10AM EST)
$59.30
-
Holiday Five Half Marathon, Day 3
Incl. $4.30 Fee
Mon 29th December 2025 (6:10AM EST)
$59.30
-
Holiday Five Half Marathon, Day 4
Incl. $4.30 Fee
Tue 30th December 2025 (6:10AM EST)
$59.30
-
Holiday Five Half Marathon, Day 5
Incl. $4.30 Fee
Wed 31st December 2025 (6:10AM EST)
$59.30
-
Holiday Five 10K, All Five Days
Incl. $11.50 Fee
Sat 27th December 2025 (7:00AM EST)
$186.50
-
Holiday Five 10K, Day 1
Incl. $3.40 Fee
Sat 27th December 2025 (7:00AM EST)
$43.40
-
Holiday Five 10K, Day 2
Incl. $3.40 Fee
Sun 28th December 2025 (7:00AM EST)
$43.40
-
Holiday Five 10K, Day 3
Incl. $3.40 Fee
Mon 29th December 2025 (7:00AM EST)
$43.40
-
Holiday Five 10K, Day 4
Incl. $3.40 Fee
Tue 30th December 2025 (7:00AM EST)
$43.40
-
Holiday Five 10K, Day 5
Incl. $3.40 Fee
Wed 31st December 2025 (7:00AM EST)
$43.40
-
Holiday Five 5K, All Five Days
Incl. $8.50 Fee
Sat 27th December 2025 (7:00AM EST)
$133.50
-
Holiday Five 5K, Day 1
Incl. $2.80 Fee
Sat 27th December 2025 (7:00AM EST)
$32.80
-
Holiday Five 5K, Day 2
Incl. $2.80 Fee
Sun 28th December 2025 (7:00AM EST)
$32.80
-
Holiday Five 5K, Day 3
Incl. $2.80 Fee
Mon 29th December 2025 (7:00AM EST)
$32.80
-
Holiday Five 5K, Day 4
Incl. $2.80 Fee
Tue 30th December 2025 (7:00AM EST)
$32.80
-
Holiday Five 5K, Day 5
Incl. $2.80 Fee
Wed 31st December 2025 (7:00AM EST)
$32.80
-
Holiday Five 50K, All Five Days
Incl. $18.50 Fee
Sat 27th December 2025 (6:00AM EST)
$368.50
-
Holiday Five 50K, Day 1
Incl. $5.50 Fee
Sat 27th December 2025 (6:00AM EST)
$80.50
-
Holiday Five 50K, Day 2
Incl. $5.50 Fee
Sun 28th December 2025 (6:00AM EST)
$80.50
-
Holiday Five 50K, Day 3
Incl. $5.50 Fee
Mon 29th December 2025 (6:00AM EST)
$80.50
-
Holiday Five 50K, Day 4
Incl. $5.50 Fee
Tue 30th December 2025 (6:00AM EST)
$80.50
-
Holiday Five 50K, Day 5
Incl. $5.50 Fee
Wed 31st December 2025 (6:00AM EST)
$80.50
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