Holiday Five
- 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
The races kick off bright and early, with the longer distances starting at 6:00 AM and the shorter races following at 7:00 AM. With a generous time limit of approximately 9.5 hours, participants can enjoy a laid-back atmosphere, focusing on the joy of running rather than competition. Though this event emphasizes a casual experience without awards or elaborate amenities, runners can expect friendly support, low entry fees, and well-marked, flat courses that are perfect for both seasoned athletes and beginners alike. Don't miss this chance to celebrate the holiday season with a rewarding challenge in the heart of Winter Park!
Organiser's Description
DESCRIPTION: Holiday Five, December 27, 28, 29, 30, 31, 2026
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, Marathon, and Half marathon6:00 am; 5K and 10K7:00 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 warned that these are low-key, bare bones, casual events. Set your expectations lowvery lowso that your disappointment will be minimal. But wait! We have easy logistics, great course, and an abundance of friendliness. Also, very 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 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 nice finishers medal, basic support (see below), a VERY generous time limit, and lots of friendly support from staff and runners. Also, convenient locations for supporters.
START/FINISH AND AID STATION: The start and finish are near the aid station a short distance from the bathrooms. The aid station 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 pickle juice.
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 an out-and-back course of approximately 2.2 miles; marathon 12 loops, half marathon 6 loops, 50K 14 loops plus 1 small lap. The 5K/10K course 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. If you don't tell us, we won't know.
CUP-LESS: Bring your own hydration devicewater 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, 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 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
