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

Get ready for an unforgettable running experience at the Holiday Five, set to take place from December 27th to December 31st, 2025, in the picturesque Winter Park, Florida! This unique event offers participants the chance to take on five different distances over five days, including a 50K, Marathon, Half Marathon, 10K, and 5K. Starting each day at the Cady Way Trail Head, 2529 Cady Way, runners can expect a friendly and low-key atmosphere, perfect for both seasoned marathoners and casual joggers alike.

The Holiday Five features a flat and partially shaded paved course that winds through the scenic trails, making it a delightful run for everyone. With generous time limits and basic support at the start/finish aid station, this event emphasizes camaraderie above all else. While you won't find age group awards or extravagant medals, you'll enjoy affordable entry fees, easy logistics, and the satisfaction of completing your chosen distance. Don’t miss this chance to kick off the New Year with a fun and challenging running event in beautiful Winter Park!

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.



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 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 for either one long race (50K, marathon, or half marathon) or for two short races (5K or 10K). 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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Location

Cady Way Trail Head, 2529 Cady Way, Winter Park, 32792, FL, United States

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Dec 27, 2025

$32.80 - $368.50