Holiday Five (Five Days, Five Distances to choose from)
Updated
Sunday, December 27, 2026, first start 6:00 AM, in Winter Park (Cady Way Trail Head). Distances: 5K, 10K, Half marathon, Marathon, 50K. Entry from $30 to $350; the 50K goes from $350 to $390 after December 20.
Course and race notes
PLACE: 2529 Cady Way, Winter Park, FL 32792.
DESCRIPTION: Holiday Five, December 27, 28, 29, 30, 31, 2026. What: 5 Distances and 5 days to choose from. 50K, Marathon, Half marathon, 10K, and 5K available each day. Where: Cady Way Trail Head, 2529 Cady Way, Winter Park, FL 32792.
In the organizer's words, from the race's own listing.
Race details
Date
Sunday, December 27
To Thursday, December 31, 2026 · in 50 days
Start time
6:00 AM
Earliest wave
Course
Trail
Dirt or single-track on at least part of the course
Distances
5K10KHalf marathonMarathon50K
Price
$30 to $350
Plus the platform's processing fee
50K goes up after Sun Dec 20 (in 43 days)
Registration
Open
Online signup closes Thu Dec 31 (in 54 days)
Opened Jan 1, 2026
Race day in Winter Park
Weather
72° / 53°F
Typical high and low for December 27, with a 25% chance of rain.
NOAA 1991–2020 climate normals, Orlando Executive Airport, FL (4.8 mi away). Averages, not a forecast; a forecast appears here a week out.
Daylight
7:16 AM – 5:35 PM
Sunrise and sunset on Sunday. The 6:00 AM start is 76 minutes before sunrise, so bring a light and something reflective.
Calculated for the race location.
Plan your trip
For the night before, Sat Dec 26
Where to stay
See all places to stay near Winter Park, FL ↗
Prices checked November 4, 2026 and can change. Confirm on the booking site before you book. We may earn a commission at no cost to you.
Getting there
- SFBOrlando Sanford International Airport12 miFlights arriving Dec 26 into SFB ↗
- MCOOrlando International Airport12 miFlights arriving Dec 26 into MCO ↗
- TPATampa International Airport87 miFlights arriving Dec 26 into TPA ↗
Prices checked November 4, 2026 and can change. Confirm on the booking site before you book. We may earn a commission at no cost to you.
Airports from OurAirports, straight-line distance. Flights open on Google Flights.
Trip cost
Add what you'll actually pay. It stays in this browser.
Total $0
Race entry starts at the lowest listed price, before the platform's fee.