Holiday Five

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

Bettie held the first Labor Day Triple in 2022 because she needed a triple that weekend. She was trying to get as many half marathons that year as she possible could and was dismayed to discover there was no triple to be found. She couldn't even find a double. In desperation, she announced a low-key, casual, no-frills event. As long as she was going to have a half marathon, might as well add a 5K, 10K, and full marathon.  The bigger-than-expected response led to all the events since, including the Holiday Five and Sunshine Double.

You might be curious why Bettie needed the runs so much in 2022. Well, Bettie likes setting goals. She first set a goal of running a marathon in all the states, then getting to 100 marathons, then getting to 300 marathons so she could get on the Mega Marathon List, then completing at least 100 marathons in a year, then moving up on the Mega Marathon List, then another 100 in a year, then becoming the third North American woman to reach 600 total marathons. When running full marathons became too much, she  switched to half marathons. At that time (2021), the most half marathons recorded in a year was 143--not too impressive. Hence, another goal:  to break that record.  She managed 156 in 2022, with help of the first Labor Day Triple.

It must be mentioned that in 2023, Bettie's good friend Debbie Del Favero surpassed the 156 in fine style by completing 213! Way to go, Debbie!

Calendar of events

We have three other events planned for next year. They are the same kind of low-key, no-frills events and in the same location as the Holiday Five. 

Sunshine Double.  First weekend in May. (May 3 and May 4, 2026).  All five distances—50K, Marathon, Half Marathon, 10K, and 5K--on both Saturday and Sunday. For more details or to register, here’s the link to the Sunshine Double: Sunshine Double  

Independence Double.  Last weekend in June (June 27 and June 28, 2026). All five distances—50K, Marathon, Half Marathon, 10K, and 5K--on both Saturday and Sunday. For more details or to register, here’s the link to the Independence Double. Independence Double

Labor Day Triple.  September 5, September 7, and September 8, 2026.  All five distances—50K, Marathon, Half Marathon, 10K, and 5K—on Saturday, Sunday, and Monday.  For more details or to register, here the link to the Labor Day Triple.  Labor Day Triple   

FAQ:

Race Start Times:  The full marathon, half marathon, and 50K start at 6:00 am. The 5K and 10K start at 7:00 am.

Bib Pickup:  Race bibs will be available at the race location starting about 45 minutes prior to race start. If you are running multiple days, you will use the same bib for all the days.

Races Not Certified:  These races are NOT certified, and therefore not Boston qualifiers.

Time Limit: All distances have a 9.5-hour time limit. This is a little "squishy," and as long as you're doing your best, we will allow you to finish, including medal and posted finish time.

Timing/Finish:  We are hand timed. We try very hard to capture your time accurately. Be sure to let us know you are finished by ringing the bell. Also, announce it to the race timer. Be sure you hear your time repeated back to you. The finish line turns off the course for a few feet to keep you out of the traffic lane when you finish.

Water/beverages:  We will have plenty of water, Gatorade, and sodas. This is a cupless race, though, so you will need a water bottle or hydration device.

Snacks:  We will provide light sweet and salty snacks. In hot weather, we will provide pickles, pickle juice, and olives.

Strollers and/or dogs are allowed, keeping in mind that the course is narrow in a few places, and you might have to yield to others. No bicycle pacing.

Parking:  There is plenty of convenient parking at the race location. You’ll probably be able to pass right by your car every lap (~2.2 miles). We'll have signs to indicate the location. Look for the Cady Way Swim Club (near Showalter Field). 

Early Start: No. We already have early start times for the longer distances, and our permit does not allow early starts.

Late Starts:  You will be allowed to start late as long as you have time to complete your event within the allotted race time. Your official time, however, begins at the start of your race distance.

Deferrals:  If you registered and find out you can’t make, contact Bettie at bettiemw@gmail.com and ask about a deferral.

Bad Weather:  We will not cancel any race unless there is imminent threat of lightening, or other life-threatening danger.

If you have any other questions, please email Bettie at bettiemw@gmail.com. 

COURSES:

There are two main courses—one for the full and half marathons, and another for the 5K and 10K. The 50K will include segments of these courses.

These courses are mostly on a paved, urban run/bike trail is flat and largely shaded. The courses are open and include two street crossings. You are responsible for crossing safely.

Marathon/half marathon course:  Twelve (12) and six (6) out-and-back laps of approximately 2.2 miles, respectively. Each lap consists of a short out-and-back through the length of the parking lot (designed to pass the restrooms) and a longer out-and-back on Cady Way Trail. There is partial shade, and passes by the aid station twice each lap.

5K and 10K course: Two (2) and four (4) laps, respectively, of approximately 1.55 miles. Each lap consists of the same parking lot out-and-back, and an out-and-back on Cady Way Trail (but not quite as far out as the half/full course).

Turn arounds for each distance will be clearly marked. The first turn-around on the trail is for the 5K/10K, and the second turn-around is for the full marathon and half marathon.

50K course:  Th 50K distance consists of fourteen (14) complete marathon laps plus two of the shorter, parking lot laps.