Holiday Five

December 27th 2026
Winter Park, FL
50 KM | 50 KM | 50 KM | 50 KM | 50 KM

WARNING: Before you continue reading, be advised these events are destined to be the worst ever. Set your expectations low—very low—so that your disappointment will be minimal. We don’t promise much, and will likely provide even less. These races are bare bones, low-key, casual events for people who want to get in just a few more runs before year-end. Or for people who want to celebrate the holidays by doing something healthy. Or for people looking for a family event during the holidays. Also, this is a great opportunity to complete your first half or full marathon. No time pressure and lots of encouragement.

YOU WILL NOT GET: a cleverly designed t-shirt or hat or socks or other apparel, great bling (actually, any bling), cute reusable race bag, spectators lining the course, crowds cheering you in, hearty food at the finish, exciting music, age group awards, or a party afterward.

YOU WILL GET:  low entry fees, courses that are guaranteed not short, a cheap finisher’s medal, a generous time limit, and published results. What more do you really need?

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. We will provide water, Gatorade, Coke, Diet Mountain Dew, and light snacks.

Courses:  All distances will start on a short lap through the parking lot and then head out onto the Cady Way Trail. This is an open course on a flat, paved, neighborhood trail. It is an open course and includes two street crossings. 

Upcoming Races

Dec 31 2026
50 KM
14 loops + 2 short loops
Multiple Loop
9:30 Cutoff
1 Elevation Rating
Flat or nearly flat
1 Surface Rating
Paved or very smooth surface
Dec 30 2026
50 KM
14 loops + 2 short loops
Multiple Loop
9:30 Cutoff
1 Elevation Rating
Flat or nearly flat
1 Surface Rating
Paved or very smooth surface
Dec 29 2026
50 KM
14 loops + 2 short loops
Multiple Loop
9:30 Cutoff
1 Elevation Rating
Flat or nearly flat
1 Surface Rating
Paved or very smooth surface
Dec 28 2026
50 KM
14 loops + 2 short loops
Multiple Loop
9:30 Cutoff
1 Elevation Rating
Flat or nearly flat
1 Surface Rating
Paved or very smooth surface
Dec 27 2026
50 KM
14 loops + 2 short loops
Multiple Loop
9:30 Cutoff
1 Elevation Rating
Flat or nearly flat
1 Surface Rating
Paved or very smooth surface

Additional Distances

This event also has the following sub ultra distances

26.2 Miles 10 KM 13.1 Miles 5 KM

Results

Date Finishers Top Result (F) Top Result (M)
12/31/25 1 6:30:01
12/30/25 9 6:15:42 6:22:35
12/29/25 3 6:22:22
12/28/25 4 5:26:27 3:37:13
12/27/25 4 10:02:39 6:11:27

Weekly Newsletter

A roundup of the week's content and most recent race results. Sent once a week on Thursday.

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