Holiday Five

PLACE

2529 Cady Way, Winter Park, FL 32792

DESCRIPTION

Holiday Five, December 27, 28, 29, 30, 31, 2026

• 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.

WHAT YOU WILL NOT GET

• Age group awards: You will not receive them.
• Great bling: Actually, any bling.
• Spectators: You won't have crowds cheering you in.
• Hearty food: No exciting food at the finish.

WHAT YOU WILL GET

• Low entry fees: Enjoy affordable participation.
• NICE finisher’s medal: Everyone loves a medal!
• Basic support: Including friendly staff and fellow runners.
• Generous time limit: Plenty of time to finish.

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, 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.

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 wingmanrunning@yahoo.com.

ORGANIZER

Wingman Running Company