Labor Day Triple (Three Days, Five Distances to choose from)
Updated
Saturday, September 4, 2027, first start 5:00 AM, in Winter Park (2529 Cady Way). Distances: 5K, 10K, Half marathon, Marathon, 50K. Entry from $30 to $205; the Half marathon goes from $55 to $65 after August 27.
Course and race notes
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).
In the organizer's words, from the race's own listing.
Race details
Date
Saturday, September 4
To Monday, September 6, 2027 · in 301 days
Start time
5:00 AM
Earliest wave
Course
Road or path
Paved course
Distances
5K10KHalf marathonMarathon50K
Price
$30 to $205
Plus the platform's processing fee
Half marathon goes up after Fri Aug 27 (in 293 days)
Registration
Open
Online signup closes Mon Sep 6 (in 303 days)
Opened Sep 7, 2026
Race day in Winter Park
Weather
91° / 75°F
Typical high and low for September 4, with a 54% chance of rain.
NOAA 1991–2020 climate normals, Orlando Executive Airport, FL (3.4 mi away). Averages, not a forecast; a forecast appears here a week out.
Daylight
7:04 AM – 7:44 PM
Sunrise and sunset on Saturday. The 5:00 AM start is 124 minutes before sunrise, so bring a light and something reflective.
Calculated for the race location.
Near the start
Pin from the race's listed address. The start line can differ; check the race website for the course map. Directions
Parking
2 public lots and garages within 0.6 mi, the nearest 0.5 mi away.
Places to eat
- McDonald's quick bite0.5 mi
- Panera Bread quick bite0.5 mi
- Dunkin' quick bite0.6 mi
- Starbucks cafe0.6 mi
Nearest public restroom: 0.1 mi from the start.
Distances are straight-line from the race address. Check the race website for official parking.
Plan your trip
For the night before, Fri Sep 3
Where to stay
2 within 3 mi17 within 5 mi
Hotel
Hotel 1 of 5: Alfond Inn Rollins
About 5 min drive1.8 mi from the start
Hotel
Hotel 2 of 5: Park Plaza Hotel
About 6 min drive2.0 mi from the start
Hotel
Hotel 3 of 5: SpringHill Suites
About 9 min drive3.0 mi from the start
Hotel
Hotel 4 of 5: Hilton Garden Inn
About 9 min drive3.0 mi from the start
Hotel
Hotel 5 of 5: Best Western Orlando East Inn & Suites
About 11 min drive3.6 mi from the start
More places on the map
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.
Places from OpenStreetMap. Straight-line distances, so times are rough.
Getting there
- MCOOrlando International Airport11 miFlights arriving Sep 3 into MCO ↗
- SFBOrlando Sanford International Airport14 miFlights arriving Sep 3 into SFB ↗
- TPATampa International Airport85 miFlights arriving Sep 3 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.