Winter Park 50K, Marathon, Half, 10K & 5K - MileBuilt Cady Way Bridge Memorial Day 3-Day Challenge
Updated
Saturday, May 29, 2027, first start 5:00 AM, in Winter Park (2535 Cady Way). Distances: 5K, 10K, Half marathon, Marathon. Entry from $35 to $70; the Marathon goes from $70 to $80 after May 14.
Course and race notes
THE COURSE. The Cady Way Bridge Memorial Day 3-Day Challenge runs on the Cady Way Trail in Winter Park, FL, on May 29-31, 2027.
The course starts and finishes at the pavilion at Cady Way Park, 2535 Cady Way, Winter Park, FL 32792.
In the organizer's words, from the race's own listing.
Race details
Date
Saturday, May 29
To Monday, May 31, 2027 · in 203 days
Start time
5:00 AM
Earliest wave
Course
Trail
Dirt or single-track on at least part of the course
Distances
5K10KHalf marathonMarathon
Price
$35 to $70
Plus the platform's processing fee
Marathon goes up after Fri May 14 (in 188 days)
Registration
Open
Online signup closes Mon May 31 (in 205 days)
Opened Jun 1, 2026
Race day in Winter Park
Weather
90° / 71°F
Typical high and low for May 29, with a 39% 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
6:28 AM – 8:16 PM
Sunrise and sunset on Saturday. The 5:00 AM start is 88 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 May 28
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 May 28 into MCO ↗
- SFBOrlando Sanford International Airport14 miFlights arriving May 28 into SFB ↗
- TPATampa International Airport85 miFlights arriving May 28 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.