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Labor Day Triple (Three Days, Five Distances to choose from)

Labor Day Triple (Three Days, Five Distances to choose from)

calendar_today September 4, 2027 location_on 2529 Cady Way, Winter Park, Central Florida 32792

About This Event

LABOR DAY TRIPLE:   September 4, September 5, and September 6, 2027 (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, Half Marathon and 50K -- 5:00 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.

WAIT! Before you register, read everything below. Here are the main points:      Races are not chip timed. We are old-fashioned hand timed.       Courses are not certified. No Boston qualifier.       No age group awards, no t-shirts, no useless bling.      Cupless—bring your own bottle

These are low-key, casual, fun events. GREAT for first timers! These are not certified or sanctioned courses—meaning, **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, cute reusable race bag, age group awards, spectators lining the course, large crowds cheering you in, hearty food at the finish, exciting music, and a party afterward.

**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 will do an out-and-back multiple times. Which means you will see other runners going and coming. Not as boring as it might sound. In fact, many people come to prefer this course design. All the courses will be on primarily paved, urban run/bike trails that are fairly flat with some to a lot of shade. These are open courses and will be open to the public. This means there may be other runners, walkers and cyclists.    -- 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 one short lap 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 7:05.)  We recommend you have a light for the first half hour.

DROP BAG: There will be a location near the start/finish line 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

Race Distances

Half Marathon
schedule 9/5/2027 05:00
Half Marathon
schedule 9/6/2027 05:00
Half Marathon
schedule 9/4/2027 05:00
10K
schedule 9/4/2027 06:00
10K
schedule 9/6/2027 06:00
10K
schedule 9/5/2027 06:00
10K
schedule 9/4/2027 06:00
5K
schedule 9/4/2027 06:00
Marathon
schedule 9/4/2027 05:00
31 Miles
schedule 9/4/2027 05:00
Marathon
schedule 9/5/2027 05:00
Marathon
schedule 9/6/2027 05:00
Marathon
schedule 9/4/2027 05:00
Half Marathon
schedule 9/4/2027 05:00
5K
schedule 9/5/2027 06:00
5K
schedule 9/6/2027 06:00
5K
schedule 9/4/2027 06:00
31 Miles
schedule 9/4/2027 05:00
31 Miles
schedule 9/5/2027 05:00
31 Miles
schedule 9/6/2027 05:00

Registration Pricing

Labor Day Triple, Marathon Day 1

$65.00

+ $4.90 processing fee

event_busy Goes up to $75.00 after Aug 28, 2027

Labor Day Triple, Marathon Day 2

$65.00

+ $4.90 processing fee

event_busy Goes up to $75.00 after Aug 28, 2027

Labor Day Triple, Marathon Day 3

$65.00

+ $4.90 processing fee

event_busy Goes up to $75.00 after Aug 28, 2027

Labor Day Triple, Marathon, all three days

$175.00

+ $11.50 processing fee

event_busy Goes up to $200.00 after Aug 28, 2027

Labor Day Triple. Half Marathon, Day 1

$55.00

+ $4.30 processing fee

event_busy Goes up to $65.00 after Aug 27, 2027

Labor Day Triple, Half Marathon, Day 2

$55.00

+ $4.30 processing fee

event_busy Goes up to $65.00 after Aug 27, 2027

Labor Day Triple, Half Marathon, Day 3

$55.00

+ $4.30 processing fee

event_busy Goes up to $65.00 after Aug 27, 2027

Labor Day Triple, Half Marathon, all three days

$145.00

+ $9.70 processing fee

event_busy Goes up to $170.00 after Aug 27, 2027

Labor Day Triple, 10K, Day 1

$40.00

+ $3.40 processing fee

event_busy Goes up to $45.00 after Aug 28, 2027

Labor Day Triple, 10K, Day 2

$40.00

+ $3.40 processing fee

event_busy Goes up to $45.00 after Aug 28, 2027

Labor Day Triple, 10K, Day 3

$40.00

+ $3.40 processing fee

event_busy Goes up to $45.00 after Aug 28, 2027

Labor Day Triple, 10K, all three days

$105.00

+ $7.30 processing fee

event_busy Goes up to $115.00 after Aug 28, 2027

Labor Day Triple, 5K, Day 1

$30.00

+ $2.80 processing fee

event_busy Goes up to $35.00 after Aug 28, 2027

Labor Day Triple, 5K, Day 2

$30.00

+ $2.80 processing fee

event_busy Goes up to $35.00 after Aug 28, 2027

Labor Day Triple, 5K, Day 3

$30.00

+ $2.80 processing fee

event_busy Goes up to $35.00 after Aug 28, 2027

Labor Day Triple, 5K, all three days

$75.00

+ $5.50 processing fee

event_busy Goes up to $85.00 after Aug 28, 2027

Labor Day Triple, 50K Day 1

$75.00

+ $5.50 processing fee

event_busy Goes up to $85.00 after Aug 28, 2027

Labor Day Triple, 50K Day 2

$75.00

+ $5.50 processing fee

event_busy Goes up to $85.00 after Aug 28, 2027

Labor Day Triple, 50K Day 3

$75.00

+ $5.50 processing fee

event_busy Goes up to $85.00 after Aug 28, 2027

Labor Day Triple, 50K all three days

$205.00

+ $13.30 processing fee

event_busy Goes up to $230.00 after Aug 28, 2027

Prices from the official registration page, updated several times a day.

Register Now

Registration links may earn us a small commission at no extra cost to you.

Weather

Frequently Asked Questions

When is Labor Day Triple (Three Days, Five Distances to choose from) 2027?
Labor Day Triple (Three Days, Five Distances to choose from) takes place on Saturday, September 4, 2027 in Winter Park, Florida.
What distances does Labor Day Triple (Three Days, Five Distances to choose from) offer?
Labor Day Triple (Three Days, Five Distances to choose from) offers Half Marathon, 10K, 5K, Marathon and 31 Miles events.
Where does Labor Day Triple (Three Days, Five Distances to choose from) take place?
Labor Day Triple (Three Days, Five Distances to choose from) is held at 2529 Cady Way in Winter Park, Florida (Central Florida). See the course maps section on this page for route details where available.
How do I register for Labor Day Triple (Three Days, Five Distances to choose from)?
Registration is online — use the Register button on this page to sign up through the race's official registration page. Registering early usually means lower entry fees.
Is there a promo code for Labor Day Triple (Three Days, Five Distances to choose from)?
Discounts are set by the race organizer and appear on the official registration page when active. The most reliable way to pay less is registering early — most Florida races raise prices as race day gets closer.

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Race Day Schedule

9/5/2027 05:00

Half Marathon Start

9/6/2027 05:00

Half Marathon Start

9/4/2027 05:00

Half Marathon Start

9/4/2027 06:00

10K Start

9/6/2027 06:00

10K Start

9/5/2027 06:00

10K Start

9/4/2027 06:00

10K Start

9/4/2027 06:00

5K Start

9/4/2027 05:00

Marathon Start

9/4/2027 05:00

31 Miles Start

9/5/2027 05:00

Marathon Start

9/6/2027 05:00

Marathon Start

9/4/2027 05:00

Marathon Start

9/4/2027 05:00

Half Marathon Start

9/5/2027 06:00

5K Start

9/6/2027 06:00

5K Start

9/4/2027 06:00

5K Start

9/4/2027 05:00

31 Miles Start

9/5/2027 05:00

31 Miles Start

9/6/2027 05:00

31 Miles Start

Registration

calendar_today September 4, 2027
location_on 2529 Cady Way, Winter Park, Central Florida 32792
directions_run 20 distances available
Register Now

Registration links may earn us a small commission at no extra cost to you.

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Labor Day Triple (Three Days, Five Distances to choose from)

September 4, 2027

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