pacertrip.

PACERTRIP CITY EDITIONUS / RACE GUIDE

Holiday Five

The city you want to run becomes your next trip.

USDec 27, 202650km · 42.195km · 21.1km +2 more events

Ebyabe · CC BY-SA 3.0

Race date in 75 days: Dec 27, 2026 Sun
City · Distance: Winter Park · 50km · 42.195km · 21.1km +2 more events
Entry fee: $30Varies by event and entry period
Status: OpenThu, January 1, 2026 ~ Sun, December 27, 2026See how to enter ↗

Official website ↗D-day as of Oct 13, 2026

About the race How to enter Course Race Prep Travel

Why you dream of this race

THE DREAM

ABOUT THE RACE

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

The race takes place over five days, from December 27 to 31, 2026.

One event is held each day, with all five distances covered.

The venue is 2529 Cady Way in Winter Park, Florida.

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.

Stories from runners who've been there.

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

No runner reports yet. We'll add them here as they come in.

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 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.

5K

Entry cost $30

until Dec 20, 2026 · subject to change — verify officially

Organizer's page

Registration platform RunSignup

Official race website Entry options

From the start line to the finish

RACE WEEK

Your 50km

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

Runners start · local timeFrom 06:00

Event	Start
Ultra50km	06:00
Marathon42.195km	06:00
Half21.0975km	06:00
10K10km	07:00
5K5km	07:00

not the start line

We have not confirmed the start line coordinates yet.

START · FINISH

Cady Way Trail Head, Winter Park, FL

Start · Google Maps

The race is divided into 9 divisions, including Holiday Five 50K, all five days,

Holiday Five 50K, Day 1, Holiday Five Marathon, all five days, and Holiday Five Marathon, Day 1.

The start takes place at Cady Way Trail Head, Winter Park, FL at 6:00 a.m. local time.

Typical race-season temperature: around 17°C (63°F): Short sleeves — hydrate for the warmth

Participant benefits

Not yet confirmed in the official race guide

To the start line,
step by step.

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

From the 2025 edition

Pick up your bib at the expo

Packet pickup information has not yet been announced.
For a small race, race-morning pickup is typical; check the registration page for details.

Stations & transport near the venue

Getting to the startNone on-site — start/finish is at Cady Way Trail Head, 2529 Cady Way, Winter Park, FL 32792
Transit cardWinter Park, FL is served by a SunRail commuter rail station connecting to downtown Orlando.

Source · checked Aug 24, 2026

More details

Getting to the start

None on-site — start/finish is at Cady Way Trail Head, 2529 Cady Way, Winter Park, FL 32792

Per prior edition (Dec 27, 2025); Nearest SunRail/Amtrak stop is the Winter Park Station in downtown Winter Park, roughly 3 miles away — best reached by car or rideshare. Suburban Orlando-area trailhead venue with no public transit directly at the site; nearest commuter rail (SunRail) and Amtrak stop is several miles away in downtown Winter Park.

Map

Getting to the finish

Same as start — small pavilion at Cady Way Trail Head (loop course)

Finish is at the same pavilion/aid station where the race starts.

Map

Transit card

Winter Park, FL is served by a SunRail commuter rail station connecting to downtown Orlando. Regular riders use the reloadable SunCard ($5 one-time cost, available at station kiosks), which uses tap-on/tap-off fare calculation with a $2.00 base fare per county plus $1.00 per additional county crossed; single-ride paper tickets are also sold at station vending machines for occasional visitors.

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.

Winter Park in December — average temperature 17°C, ideal for chasing a fast time.

Your body temperature can drop quickly while waiting at the start, so wear a disposable outer layer and remove it just before the gun.

Public transport does not reach the venue.

A private car or rental car is the only practical way to get there.

Registration is handled through the RunSignup platform.

For full marathon, the race really begins after 30 km.

It is better to pass halfway 5–10 seconds slower than your target pace to help you maintain your pace later,

and start taking gels early, before you feel hungry.

The start is early, at 06:00.

Counting back from waking up, breakfast and travel, staying near start line the night before is more convenient.

Registration is open until December 27, 2026.

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.

The Alfond Inn

Hotel · 3.1km

9.3/10(189)

View on Booking.com

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

Winter Park: Flavors of Winter Park gourmet walking tour

$69

View on GetYourGuide

Orlando ICON Park Full-Day Guided Tour

$145

Holiday Five

About Holiday Five — what makes it special

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

The road to your own record

When the city cheers

The trip that follows the run

Holiday Five runner reviews and race reports

Stories from runners who've been there.

See it on video,feel it through their stories.

How to enter Holiday Five — registration routes

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

5K

Holiday Five course map and elevation

Your 50km

Cady Way Trail Head, Winter Park, FL

Participant benefits

Where and when to collect your Holiday Five race bib

To the start line,step by step.

Pick up your bib at the expo

Stations & transport near the venue

Getting to the start

Getting to the finish

Transit card

From race morning to after the finish.

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

The Alfond Inn

Winter Park car rental (EconomyBookings)

Winter Park: Flavors of Winter Park gourmet walking tour

Orlando ICON Park Full-Day Guided Tour

House close Baldwin-park Lake & Downtown Orlando

Orlando｜Private Airport Pickup/Drop-off Service from Orlando Executive Airport

Kennedy Space Center Visitor Complex Highlights Orlando Tour

Hotels near the Holiday Five start line in Winter Park

Hotels that make race morning easy

The Alfond Inn

House close Baldwin-park Lake & Downtown Orlando

10 Minutes from Universal - Relaxing Guest Suite

1BR 1BA in Historic Park Ave Home

The Pineapple Express

Light and Easy Getaways

Pretige Studio

Time for you, before and after the finish

Winter Park car rental (EconomyBookings)

Orlando｜Private Airport Pickup/Drop-off Service from Orlando Executive Airport

Orlando｜Private Airport Pickup/Drop-off Service from Orlando International Airport

Melbourne｜Private airport pickup/drop-off service from Melbourne Airport

Orlando Go Card - All-Inclusive Pass

The Orlando Eye Combo Ticket

Orlando SeaWorld Theme Park Admission Ticket

Wild Florida Wildlife Park Admission Ticket, Orlando

Orlando Bike Tour: A Guided Tour to Discover the Real Orlando

Winter Park: Chain of Lakes Clear Kayak Tour

Orlando Urban Clear Kayak or Paddleboard Paradise Tour

Paddleboarding or Clear Kayaking Experience with Dogs in Orlando

2-Hour Clear Kayak & Paddleboard Rental in Orlando

Date Night LED Clear Kayaking or Paddleboarding Experience in Orlando

Sunset Clear Kayaking or Clear Paddleboarding Experience in Orlando

Where runners eat in Winter Park

Eating well is part of the trip

Winter Park: Flavors of Winter Park gourmet walking tour

What to see in Winter Park after the race

Seeing Winter Park with the medal on

Orlando ICON Park Full-Day Guided Tour

Kennedy Space Center Visitor Complex Highlights Orlando Tour

Total cost and budget for Holiday Five

Trip prep too,light and in one place.

Runner stories and questions about Holiday Five

With runners who dream ofthe same start line.

Frequently asked questions about Holiday Five

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

See it on video,
feel it through their stories.

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

To the start line,
step by step.

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

Trip prep too,
light and in one place.

With runners who dream of
the same start line.