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Holiday Five

Sun, Dec 27, 2026, 6:00 AM EST

Location
Winter Park, FL
Cady Way Trail Head, 2529 Cady Way, 32792
Type
RUN

Sign up and verify details on the organizer’s official page.

Vibe analysis coming soon

Course feel, difficulty, and community fit are being added to this listing. Check back, and always confirm details on the official registration page.

At a glance

Who it's for

  • Beginner Friendly

Great for: beginners

Perks & features

  • Awards
  • Free
  • Swag Included

From the public listing — confirm on the official site.

Auto-drafted from the public listing — confirm details on the official event page before signing up.

Distances & registration

30 options

Registration for all distances is through the official signup link above.

  • 3.1 Miles

    Sun, Dec 27, 7:00 AM EST · From $133.50

    Opens Jan 7, 2026, 5:27 AM EST · Closes Dec 20, 2026, 6:59 PM EST

  • 3.1 Miles

    Sun, Dec 27, 7:00 AM EST · From $32.80

    Opens Jan 7, 2026, 5:27 AM EST · Closes Dec 20, 2026, 6:59 PM EST

  • 3.1 Miles

    Mon, Dec 28, 7:00 AM EST · From $32.80

    Opens Jan 7, 2026, 5:27 AM EST · Closes Dec 20, 2026, 6:59 PM EST

+ 27 more options
  • 3.1 Miles

    Tue, Dec 29, 7:00 AM EST · From $32.80

    Opens Jan 7, 2026, 5:27 AM EST · Closes Dec 20, 2026, 6:59 PM EST

  • 3.1 Miles

    Wed, Dec 30, 7:00 AM EST · From $32.80

    Opens Jan 7, 2026, 5:27 AM EST · Closes Dec 20, 2026, 6:59 PM EST

  • 3.1 Miles

    Thu, Dec 31, 7:00 AM EST · From $32.80

    Opens Jan 7, 2026, 5:27 AM EST · Closes Dec 20, 2026, 6:59 PM EST

  • 6.2 Miles

    Sun, Dec 27, 7:00 AM EST · From $186.50

    Opens Jan 7, 2026, 5:27 AM EST · Closes Dec 20, 2026, 6:59 PM EST

  • 6.2 Miles

    Sun, Dec 27, 7:00 AM EST · From $43.40

    Opens Jan 7, 2026, 5:27 AM EST · Closes Dec 20, 2026, 6:59 PM EST

  • 6.2 Miles

    Mon, Dec 28, 7:00 AM EST · From $43.40

    Opens Jan 7, 2026, 5:27 AM EST · Closes Dec 20, 2026, 6:59 PM EST

  • 6.2 Miles

    Tue, Dec 29, 7:00 AM EST · From $43.40

    Opens Jan 7, 2026, 5:27 AM EST · Closes Dec 20, 2026, 6:59 PM EST

  • 6.2 Miles

    Wed, Dec 30, 7:00 AM EST · From $43.40

    Opens Jan 7, 2026, 5:27 AM EST · Closes Dec 20, 2026, 6:59 PM EST

  • 6.2 Miles

    Thu, Dec 31, 7:00 AM EST · From $43.40

    Opens Jan 7, 2026, 5:27 AM EST · Closes Dec 20, 2026, 6:59 PM EST

  • 13.1 Miles

    Sun, Dec 27, 6:00 AM EST · From $263.50

    Opens Jan 7, 2026, 5:27 AM EST · Closes Dec 20, 2026, 6:59 PM EST

  • 13.1 Miles

    Sun, Dec 27, 6:00 AM EST · From $59.30

    Opens Jan 7, 2026, 5:27 AM EST · Closes Dec 20, 2026, 6:59 PM EST

  • 13.1 Miles

    Mon, Dec 28, 6:00 AM EST · From $59.30

    Opens Jan 7, 2026, 5:27 AM EST · Closes Dec 20, 2026, 6:59 PM EST

  • 13.1 Miles

    Tue, Dec 29, 6:00 AM EST · From $59.30

    Opens Jan 7, 2026, 5:27 AM EST · Closes Dec 20, 2026, 6:59 PM EST

  • 13.1 Miles

    Wed, Dec 30, 6:00 AM EST · From $59.30

    Opens Jan 7, 2026, 5:27 AM EST · Closes Dec 20, 2026, 6:59 PM EST

  • 13.1 Miles

    Thu, Dec 31, 6:00 AM EST · From $59.30

    Opens Jan 7, 2026, 5:27 AM EST · Closes Dec 20, 2026, 6:59 PM EST

  • 26.2 Miles

    Sun, Dec 27, 6:00 AM EST · From $316.00

    Opens Jan 7, 2026, 5:27 AM EST · Closes Dec 20, 2026, 6:59 PM EST

  • 26.2 Miles

    Sun, Dec 27, 6:00 AM EST · From $69.90

    Opens Jan 7, 2026, 5:27 AM EST · Closes Dec 20, 2026, 6:59 PM EST

  • 26.2 Miles

    Mon, Dec 28, 6:00 AM EST · From $69.90

    Opens Jan 7, 2026, 5:27 AM EST · Closes Dec 20, 2026, 6:59 PM EST

  • 26.2 Miles

    Tue, Dec 29, 6:00 AM EST · From $69.90

    Opens Jan 7, 2026, 5:27 AM EST · Closes Dec 20, 2026, 6:59 PM EST

  • 26.2 Miles

    Wed, Dec 30, 6:00 AM EST · From $69.90

    Opens Jan 7, 2026, 5:27 AM EST · Closes Dec 20, 2026, 6:59 PM EST

  • 26.2 Miles

    Thu, Dec 31, 6:00 AM EST · From $69.90

    Opens Jan 7, 2026, 5:27 AM EST · Closes Dec 20, 2026, 6:59 PM EST

  • 31 Miles

    Sun, Dec 27, 6:00 AM EST · From $368.50

    Opens Jan 1, 2026, 11:56 AM EST · Closes Dec 20, 2026, 6:59 AM EST

  • 31 Miles

    Sun, Dec 27, 6:00 AM EST · From $80.50

    Opens Jan 1, 2026, 11:56 AM EST · Closes Dec 20, 2026, 6:59 PM EST

  • 31 Miles

    Mon, Dec 28, 6:00 AM EST · From $80.50

    Opens Jan 1, 2026, 11:56 AM EST · Closes Dec 20, 2026, 6:59 PM EST

  • 31 Miles

    Tue, Dec 29, 6:00 AM EST · From $80.50

    Opens Jan 1, 2026, 11:56 AM EST · Closes Dec 20, 2026, 6:59 PM EST

  • 31 Miles

    Wed, Dec 30, 6:00 AM EST · From $80.50

    Opens Jan 1, 2026, 11:56 AM EST · Closes Dec 20, 2026, 6:59 PM EST

  • 31 Miles

    Thu, Dec 31, 6:00 AM EST · From $80.50

    Opens Jan 1, 2026, 11:56 AM EST · Closes Dec 20, 2026, 6:59 PM EST

Vibe Check

Steady Effort

Flat road course

Based on terrain, weather, and distance data.

The course

From the organizer

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, Marathon, and Half marathon—6:00 am; 5K and 10K—7:00 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 low—very low—so that your disappointment will be minimal. But wait! We have easy logistics, great course, and an abundance of friendliness. Also, very convenient parking—pass your car every lap. If you’re still interested, here’s 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 finisher’s 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 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, 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 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 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.

Cupless :  Bring your own hydration device—water 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 Bettie at bettiemw@gmail.com.

BMW Running Company

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