calendar_today 01 May, 2027 – 02 May, 2027
directions_run Running
language Official Website
sell $30.00 – $140.00
STOP! Read more before you sign up. These events are no frills, low-key, casual, but FUN events. Great for first timers. Convenient parking, both for the runner and for supporters. These are NOT certified courses—meaning, among other thing, NOT a Boston qualifier. Don’t expect much fancy stuff. Our basics are outstanding, though.
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, hot food at the finish, exciting music, and a party afterward, all on a certified course. There are plenty of other events that have those things.
You DO get: low entry fees (which is why you don't get that other stuff), convenient parking, courses that are guaranteed not short, a simple-but-nice finisher’s medal, a generous time limit, and a published finish time. But isn’t that all you really need? You know you want to sign up.
COURSES: The courses are lap courses, meaning that you’ll do a short loop multiple times. Not as boring as it might sound because you’ll see other runners going and coming, and you pass the start/finish and bathrooms each lap. The paved, urban run/bike trail is flat and largely shaded. These are open courses, and include two street crossings each lap. You are responsible for crossing safely. More course details can be found under Detailed Course Descriptions above.
-- The lap for the marathon, half marathon, and 50K is approximately 2.2 miles. The full marathon is twelve laps, the half is six laps, and the 50K is fourteen laps plus two short laps at the end.
-- The lap for the 5K and 10K is approximately 1.55 miles—two laps for the 5K and four laps for the 10K.
Turn-arounds for each distance will be clearly marked. We will have rubber bands to help you keep track of your laps.
START / FINISH / AID STATION: The only aid station is at the start/finish location, which you will pass twice each lap. We will provide chilled water, Gatorade, soda, and sweet and salty snacks.
CUPLESS: This is a cupless race. Meaning we would like for you to bring your own hydration device—water bottle, hydration belt/pack. There will be a table for your water bottles. We'll have small paper cups, but you'd be better off with your own bottle(s).
HEAT: Florida is typically hot and humid. We will provide ice for your water, Gatorade, and soda. There will also be a bucket of ice water for you to dip your hat, cooling towel, etc. We will have pickles and pickle juice, as well as a variety of salty snacks.
BATHROOMS: The bathrooms are a little walk from the start/finish, but you’ll pass them during each lap. They're inside, permanent structure bathrooms with soap and water!
LIGHT: It will be just starting to break daylight at the start, but still dark in places on the course. (Sunrise is at 6:44.) We recommend you have a light for the first half hour.
DROP BAG: The start/finish is in a small pavilion, where you may leave a drop bag.
FINISH LINE: When you finish, ring the bell, or be sure to let the timer know you’re finished. Without this, you won’t get a finish time—or at least not an accurate time. Remember we are hand-timed—no timing chips! We won't know to record your time if you don't tell us you're done.
NOW, 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 marathons completed. Think four-digit numbers. Just imagine the stories! These experienced runners love to meet new runners and offer encouragement and wisdom.
VOLUNTEERS: We always need volunteers. Each full volunteer day earns a free long run (half marathon or full marathon) or two short runs (5K or 10K). Email at wingmanrunning@yahoo.com
Wingman Running Company
May 01, 2027
Distance — 49.9K
Type — Running
06:00
$75.00
May 01, 2027
Distance — 21.1K
Type — Running
06:00
$55.00
May 01, 2027
Distance — 21.1K
Type — Running
06:00
$100.00
May 01, 2027
Distance — 42.2K
Type — Running
06:00
$65.00
May 01, 2027
Distance — 42.2K
Type — Running
06:00
$120.00
May 01, 2027
Distance — 49.9K
Type — Running
06:00
$140.00
May 01, 2027
Distance — 10K
Type — Running
07:00
$40.00
May 01, 2027
Distance — 10K
Type — Running
07:00
$70.00
May 01, 2027
Distance — 5K
Type — Running
07:00
$30.00
May 01, 2027
Distance — 5K
Type — Running
07:00
$50.00
May 02, 2027
Distance — 49.9K
Type — Running
06:00
$75.00
May 02, 2027
Distance — 21.1K
Type — Running
06:00
$55.00
May 02, 2027
Distance — 42.2K
Type — Running
06:00
$65.00
May 02, 2027
Distance — 10K
Type — Running
07:00
$40.00
May 02, 2027
Distance — 5K
Type — Running
07:00
$30.00
These values represent the 3-year monthly averages for May in Winter Park.
Learn more about the host city, Winter Park.
Winter Park is a city of 31,000 people (2019) in Florida near Orlando. Winter Park is often seen as a popular tourist destination for those visiting Orlando that want an escape from the typical tourist scene of the Orlando theme parks. There is a quaint, local feel to the suburb even though there are a lot of tourists, especially during the winter months and holidays.
Read more launchTours and activities near Winter Park, powered by Viator.
Watch highlights and course previews from previous years.
Read what other athletes have to say about their experience at the Sunshine Double.
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location_on Orlando, Florida, US
calendar_today Oct 24, 2026
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