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PACERTRIP CITY EDITIONUS / RACE GUIDE
Labor Day Triple race photo

Labor Day Triple

The city you want to run becomes your next trip.

Labor Day Triple race photoWinter Park
US
Ebyabe · CC BY-SA 3.0Grand Canyon National Park · CC BY 2.0
Race date in 331 days
Sep 4, 2027 Sat
City · Distance
Winter Park · 50km · 42.195km · 21.1km +2 more events
Entry fee
$65Varies by event and entry period
2027Date Sep 4, 2027 · Open
2026
2026Date Sep 5, 2026 · Entry fee $30 · Start 05:00
Official website ↗D-day as of Oct 8, 2026
Labor Day Triple race photo
Ebyabe · CC BY-SA 3.0
Labor Day Triple race photo
Grand Canyon National Park · CC BY 2.0
About the raceRunner storiesHow to enterCourseRace PrepTravel
Why you dream of this race

THE DREAM

About Labor Day Triple — what makes it special

ABOUT THE RACE

A day you'll remember,
long past the finish line.

The event takes place over the three-day Labor Day weekend, September 5, 6, and 7, 2026.

The venue is the Cady Way Park trailhead in Winter Park, Florida.

Five distances — 50K, full marathon, half marathon, 10K, and 5K — are offered each day, and the schedule repeats for all three days.

The road to your own record

Picture the course in advance
and find the pace that fits you.

When the city cheers

Streets lined with cheers, runners all around.
You'll be part of that scene.

The trip that follows the run

Take it slow with the finish still in you,
and meet the city all over again.

Labor Day Triple runner reviews and race reports

Stories from those who ran it first.

From the joy of finishing to the tough moments — read what runners wrote themselves.

Race reports: 1
Olivia Medina
“Three marathons in three days is now my new streak, and I’m already looking forward to training for five in a row.”

The runner completed marathons on 3 consecutive days at the Labor Day Triple. Legs began hurting at mile 18 on day two, but changes to shoes and carried gear, along with good fueling, helped make the final day a strong run.

Read the original on Maniacs Fanatics Madness

We translated a short line from each public race report and summarized the experience. Finish times are as stated by the author, and past editions may differ from this year's weather and operations.

See it on video,
feel it through their stories.

Preview the course and read what runners who went before you wrote.

We haven't found a video for this race yet. We'll add one when we do.

The way in that fits you

YOUR ENTRY

How to enter Labor Day Triple — registration routes

How to reach the start line —
start with what fits you.

Here are the ways to enter and what each requires.
Check the organizer's page for whether entries are open.

Marathon

Entry cost $65

until Aug 28, 2027 · subject to change — verify officially

Organizer's page

5K

Entry cost $30

until Aug 28, 2027 · subject to change — verify officially

Organizer's page

Registration platform RunSignup

Official race websiteEntry options
From the start line to the finish

RACE WEEK

Labor Day Triple course map and elevation

The 50km I'll run

Know the course and time limit, and race day comes into focus.

Runners start · local timeFrom 05:00
EventStart
Ultra50km05:00
Marathon42.195km05:00
Half21.0975km05:00
10K10km06:00
5K5km06:00
START · FINISH

2529 Cady Way, Winter Park, FL

Start · Google Maps
Show more

The race categories are Labor Day Triple, Marathon Day 1·Labor Day Triple.

Half Marathon, Day 1·Labor Day Triple, 10K, Day 1·Labor Day Triple, 10K, and all three days, among eight categories.

The start is at 2529 Cady Way, Winter Park, FL, at 5:00 AM local time.

Course is a loop course that returns to the starting point.

Typical race-season temperature: around 26°C (79°F)
Hot race — plan fluids and electrolytes

Participant benefits

Not yet confirmed in the official race guide

Where and when to collect your Labor Day Triple race bib

To the start line,
step by step.

Pick up your bib, check your wave.
So on race morning, you can just run.

From the 2026 edition

Stations & transport near the venue

  • Getting to the startNo public transit; start is at Cady Way Park (Trailhead), 2529 Cady Way, Winter Park, FL 32792
  • IC cardWinter Park has its own SunRail commuter rail station (also an Amtrak stop) using a tap-on/tap-off system;…

Source · checked Aug 24, 2026

More details

Getting to the start

No public transit; start is at Cady Way Park (Trailhead), 2529 Cady Way, Winter Park, FL 32792

Official runsignup page confirms start at Cady Way Park trailhead. Car access only — suburban park setting, no nearby transit station.

Parking available on-site at Cady Way Park with overflow parking nearby and a school across the street. Event described as "no frills, low-key, casual" with hand-timing (ring the bell at finish).

Map

Getting to the finish

Cady Way Park (same as start — loop course)

Loop-course event; finish is at the same Cady Way Park location as the start.

Map

Start shuttle

No shuttle bus service; this is a low-key, hand-timed loop event.

IC card

Winter Park has its own SunRail commuter rail station (also an Amtrak stop) using a tap-on/tap-off system; a SunCard or single ticket is bought at the station's Ticket Vending Machine, with round trips around $7.50. SunRail mainly serves the Orlando commuter corridor, so a car or rideshare is still needed to reach race venues directly.

Source · checked Aug 24, 2026
READY TO RUN

From race morning to after the finish.

Your start time, fuel and bag drop.
Know them ahead and the run feels easier.

Winterpark in September reaches an average high of 26°C.

Heat quietly takes time off a result.

Start pace one level easier than planned, and stop at aid station before thirst sets in.

A hat and sunscreen are essential gear.

Public transportation does not reach the venue.

A private or rental car is the practical option.

Registration is handled through the RunSignup platform.

Full marathon really begins after 30km.

Passing halfway 5~10 seconds slower than the target pace gives the second half a better chance of holding together,

and gels should start early, before hunger appears.

The 05:00 start is early.

Counting backward from wake-up, breakfast, and travel, a room near start line will make race morning easier.

Times are local to Winter Park. Check the latest official information before the race.

A trip built around the race

STAY A LITTLE

MAKE IT A RUNTRIP

The race is one day,
the trip can be longer.

From a hotel that makes race morning easy,
to the meals and views you'll enjoy with the medal on.

Winter Park car rental (EconomyBookings)

Compare rates from various rental car companies, self-drive (price confirmed at time of reservation) · Make reservation after checking price

View on EconomyBookings

Hotels near the Labor Day Triple start line in Winter Park

Hotels that make race morning easy

View all →

Distances are straight-line from the start/finish area.
Check real travel times and booking terms with each hotel.

The start and finish are in the same place
We picked stays around that one spot.

House close Baldwin-park Lake & Downtown Orlando

Accommodation · 2.6km

9.2/10(14)
View on Booking.com

Swipe sideways to see more hotels.

Time for you, before and after the finish

View all →

Rest a little, wander a little.
Pick what suits you and whoever you're with.

Winter Park car rental (EconomyBookings)

Compare rates from various rental car companies, self-drive (price confirmed at time of reservation) · Make reservation after checking price

View on EconomyBookings

Where runners eat in Winter Park

Eating well is part of the trip

View all →

A meal before the race, a dinner to celebrate the finish.

Seeing Winter Park with the medal onThe city you ran — this time, a little slower.View on map

Hotel distances are straight-line from the start. Experiences, food and sights are travel products in Winter Park.

Total cost and budget for Labor Day Triple

TRAVEL ESSENTIALS

Trip prep too,
light and in one place.

ChecklistLocal eSIM · YesimFlight delay or cancellation compensation · AirHelpPace calculator

Once saved, you can open this page without an internet connection

Runner stories and questions about Labor Day Triple

RUN TOGETHER

With runners who dream of
the same start line.

Be the first runner
Leave this room's first post

Winter Park runners' room

Frequently asked questions about Labor Day Triple

FAQ
When does Labor Day Triple 2027 take place?

It takes place on Sat, September 4, 2027 in Winter Park, FL, United States.

How much is the Labor Day Triple 2027 entry fee?

The main event costs $65.

What distances does Labor Day Triple 2027 offer?

Marathon · Half · 10K · 5K · Ultra.

What time does Labor Day Triple 2027 start?

The race starts at 05:00.

Where does Labor Day Triple 2027 start?

2529 Cady Way, Winter Park, FL.

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