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 Marathon, Half Marathon, 10km, 5km, Ultra

Event summary

Join us for the Holiday Five, an exciting multi-day running event taking place from December 27 to December 31, 2025, in the beautiful Winter Park, Florida. This festive gathering at the Cady Way Trail Head invites runners of all levels to tackle five different race distances over five consecutive days: a challenging 50K, a full Marathon, a Half Marathon, a 10K, and a 5K. Each race will kick off at the crack of dawn, with the 50K and Marathon starting at 6:00 am, followed by the Half Marathon at 6:10 am, and the 5K and 10K at 7:00 am.

The scenic, paved course is perfect for those looking to set personal records or simply enjoy a fun day out on the trails. With a generous time limit of 9.5 hours, you can take your time and soak in the vibrant atmosphere. While the event embraces a low-key, casual vibeβ€”complete with basic amenities and no frillsβ€”participants can expect friendly support and easy logistics throughout the event. So grab your running shoes, bring your own hydration device, and get ready to celebrate the joy of running at the Holiday Five!

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 (or so)

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

N 28.59458, W -081.31670



WARNING: Before you continue, be aware 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 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 simple 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 50K/marathon/half marathon course is a double out-and-back loop of approximately 2.2 miles; marathon 12 loops, half marathon 6 loops, 50K 14 loops plus 2 "baby" loops. The 5K/10K courses 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.

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].

BMW Running Company

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