The Labor Day Triple takes place in Winter Park, Florida, at 2529 Cady Way, offering runners multiple distance options on September 5, 2026. You can compete in a 1-mile run, a 10K, a half marathon, or a full marathon. All events start at 5:00 AM. Entry fees range from $30 to $230 depending on the distance selected. This multi-distance format allows you to choose based on your training and goals while racing in the same event. Winter Park's central Florida location makes it accessible for regional travel, and the early morning start is typical for endurance events in the area's warm climate. Whether you're looking for a short distance or the full marathon challenge, the Labor Day Triple accommodates various fitness levels within a single race weekend.
From the Race Organizer
LABOR DAY TRIPLE: September 5, September 6, and September 7, 2026 (Labor Day Weekend) PLACE: Cady Way Park (Trailhead), 2529 Cady Way, Winter Park, FL 32792 WHAT: Labor Day Triple--50K, Marathon, Half marathon, 10K, and 5K each day (Five distance for three days. Yes, people do run three days consecutively) START TIMES: Marathon and 50K -- 5:00 am; Half Marathon -- 5:10 am; 5K and 10K -- 6:00 am TIME LIMIT: 9 hours (or so) PARKING: Cady Way Park. GPS coordinates: N 28.59458, W -081.31670. Also, there is an overflow parking lot nearby and a school across the street. All locations are convenient. WARNING: Before you register, Read everything below. Here are the main points: Not chip-timed. We are hand-timed. Let us know when you finish. Courses not certified. Not designed for speed. NOT a Boston qualifier. No age group awards, no t-shirts, no bling. Cupless—bring your own bottle. For 50K, marathon and half marathon you’ll need a light Now, if you haven’t tuned out yet, be advised these events are no frills, low-key, casual, fun events. GREAT for first timers, maybe not so great for a PR. This is not a certified or sanctioned course— NOT a Boston qualifier. Don’t expect much and maybe you won’t be disappointed. WHAT YOU DON’T GET: t-shirt, hat, socks, or any other apparel, great bling (actually, any bling), cute reusable race bag, age group awards, spectators lining the course, crowds cheering you in, hearty food at the finish, exciting music, and a party afterward, all on a certified course. There are plenty of other events out there for you. WHAT YOU DO GET: low entry fees, courses that are guaranteed not short, a simple finisher’s medal, a generous time limit, and a published finish time. But isn’t that all you really need? What do you do with all that other stuff anyway? You know you want to sign up. Really, where else can you run a marathon for $65? COURSES: The courses are NOT certified--no Boston qualifier here. The courses are lap courses, meaning that you’ll do a double out-and-back multiple times. Which means you’ll see other runners going and coming. Not as boring as it might sound. In fact, many people come to prefer this course design. The paved, urban run/bike trail is flat and largely shaded. This is an open course, and includes two street crossings each lap. You are responsible for crossing safely. See Detailed Course Descriptions above for more details. The marathon and half marathon lap is approximately 2.2 miles. The full is twelve laps and the half is six laps. The 5K and 10K lap is approximately 1.55 miles—two laps for the 5K and four laps for the 10K. The 50K is fourteen marathon laps, with two small laps added at the end. Turn arounds for each distance will be clearly marked. Rubber bands will be available to help you keep track of your laps. For more details and a crude course map, see Detailed Course Description above. FINISH: When you finish, be sure to ring the bell and make sure the timer knows you are finished. Otherwise, you won't get an accurate time. Remember we are hand-timed. AID STATION: The aid station is at the start/finish of the loop course, which you will pass two times each lap. We will provide plenty of water, Gatorade, and soda, along with a variety of sweet and salty snacks. This is a cupless race. Bring your own hydration device—water bottle, hydration belt/pack. HEAT: Florida is typically hot and humid. We will provide ice for your water/Gatorade, hat, water bottle, etc. We will also have ice water in a bucket for you to dip your hat, cooling towel, etc. We will also have pickles, olives, and pickle juice, as well as a variety of salty snacks. LIGHT: Marathoners, 50Kers, and half marathoners will need a light for the first couple of hours. It won’t get light until around 6:40. BATHROOMS: The bathrooms are a little walk from the start/finish, but you’ll pass them during each lap. DROP BAG: The start/finish is in a small pavilion, where you may leave a drop bag. If you are still undecided (congratulations for reading this far), and you want to know what to expect, we won’t likely have world class athletes based on speed, but we will likely have world class athletes based on numbers of marathon completed. We have had at least five people who are at the top of the Mega Marathon List. Think four-digit numbers. Just imagine the stories! VOLUNTEERS: We always need volunteers. Each volunteer day earns one free race entry for a long distance (50K, marathon, half marathon), or two free entries for a short distance (5K or 10K). Contact Steve or Sue at wingmanrunning@yahoo.com. You may use the free entry yourself or for someone else. Wingman Running Company
