Holiday Five 2026 — Winter Park, FL

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. 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 wingmanrunning@yahoo.com Wingman Running Company