calendar_today 29 May, 2027 – 31 May, 2027
directions_run Running
language Official Website
sell $35.00 – $85.00
The 3-Day Memorial Day Bridge Challenge runs on Cady Way Trail in Winter Park, FL on May 29–31, 2027. A modified out-and-back on an accessible, measured trail. Every distance opens with a prologue, then locks into repeats. Every repeat brings you back to the SR 436 bridge — 685 feet of elevated asphalt over Semoran Blvd. It does not get easier. It gets familiar. That is the point.
Five distances: 5K · 10K · Half Marathon · Marathon · 50K. Core distances run both days. 50K is confirmed for this event.
START TIMES
5:00 AM — Marathon and 50K
5:10 AM — Half Marathon
6:00 AM — 5K and 10K
RACE DAY CUTOFF
2:00 PM. This applies to the full race day — not per distance. Runners still on course after the cutoff will be directed off course.
PARKING
Cady Way Park, 2535 Cady Way, Winter Park, FL 32792. Use the central lot or the overflow lot west of the Cady Way pool — both open early. The cul-de-sac and pool lots fill later. Arrive early.
AID STATION
Cupless event. Carry your own fluids — handheld bottle, vest, or waist pack. MileBuilt provides water, an electrolyte drink, and basic snacks. Do not rely on the aid station as your complete nutrition plan, especially for longer distances or multi-day participation.
BIB PICKUP
Available on race day beginning one hour before your scheduled start time — honor system, no ID required. A friend may pick up on your behalf. No bib transfers.
BARE-BONES EVENT
No shirts. No race bags. No expo.
FINISH
Not chip timed. When you finish: cross the line, strike the GONG, then complete the Clock Out at the MileBuilt Time Clock. Official finish times are recorded at the MileBuilt Time Clock and verified by the Race Director before results are posted. Every runner must complete the Clock Out process to receive an official finish record.
May 29, 2027
Distance — 50K
Type — Running
05:00
$85.00
May 29, 2027
Distance — 42.2K
Type — Running
05:00
$70.00
May 29, 2027
Distance — 21.1K
Type — Running
05:10
$60.00
May 29, 2027
Distance — 10K
Type — Running
06:00
$45.00
May 29, 2027
Distance — 5K
Type — Running
06:00
$35.00
May 30, 2027
Distance — 50K
Type — Running
05:00
$85.00
May 30, 2027
Distance — 42.2K
Type — Running
05:00
$70.00
May 30, 2027
Distance — 21.1K
Type — Running
05:10
$60.00
May 30, 2027
Distance — 10K
Type — Running
06:00
$45.00
May 30, 2027
Distance — 5K
Type — Running
06:00
$35.00
May 31, 2027
Distance — 50K
Type — Running
05:00
$85.00
May 31, 2027
Distance — 42.2K
Type — Running
05:00
$70.00
May 31, 2027
Distance — 21.1K
Type — Running
05:10
$60.00
May 31, 2027
Distance — 10K
Type — Running
06:00
$45.00
May 31, 2027
Distance — 5K
Type — Running
06:00
$35.00
These values represent the 3-year monthly averages for May in Winter Park.
Learn more about the host city, Winter Park.
Winter Park is a city in Orange County, Florida, United States. The population was 29,795 at the 2020 census. It is part of the Orlando metropolitan area.
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