MileBuilt 3-Day Memorial Day Bridge Challenge
About this race
THE RACE
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.
Pick your distance
Trail running
50K - Day 1 (Saturday)
50K The 3-Day Bridge Challenge runs on Cady Way Trail in Winter Park, FL. Start and finish at the pavilion at Cady Way Park. The 50K opens with a prologue that sets your total distance, then locks into 10 repeats. Every repeat is the same: a cul-de-sac near the tennis and pickleball courts, then out along the trail to a Forsyth Road turnaround. That's 20 bridge climbs. Every repeat crosses the SR 436 bridge: 685 feet of elevated asphalt rising over Semoran Blvd. It climbs. It descends. You come back to it every time. That is the point. Runners may access their own vehicle if parked along the course. Distances and Start Times 5:00 AM — Marathon and 50K 5:10 AM — Half Marathon 6:00 AM — 5K and 10K
50K - Day 2 (Sunday)
50K The 3-Day Bridge Challenge runs on Cady Way Trail in Winter Park, FL. Start and finish at the pavilion at Cady Way Park. The 50K opens with a prologue that sets your total distance, then locks into 10 repeats. Every repeat is the same: a cul-de-sac near the tennis and pickleball courts, then out along the trail to a Forsyth Road turnaround. That's 20 bridge climbs. Every repeat crosses the SR 436 bridge: 685 feet of elevated asphalt rising over Semoran Blvd. It climbs. It descends. You come back to it every time. That is the point. Runners may access their own vehicle if parked along the course. Distances and Start Times 5:00 AM — Marathon and 50K 5:10 AM — Half Marathon 6:00 AM — 5K and 10K
50K - Day 3 (Monday)
50K The 3-Day Bridge Challenge runs on Cady Way Trail in Winter Park, FL. Start and finish at the pavilion at Cady Way Park. The 50K opens with a prologue that sets your total distance, then locks into 10 repeats. Every repeat is the same: a cul-de-sac near the tennis and pickleball courts, then out along the trail to a Forsyth Road turnaround. That's 20 bridge climbs. Every repeat crosses the SR 436 bridge: 685 feet of elevated asphalt rising over Semoran Blvd. It climbs. It descends. You come back to it every time. That is the point. Runners may access their own vehicle if parked along the course. Distances and Start Times 5:00 AM — Marathon and 50K 5:10 AM — Half Marathon 6:00 AM — 5K and 10K
Running
Marathon - Day 1 (Saturday)
Marathon The 3-Day Bridge Challenge runs on Cady Way Trail in Winter Park, FL. Start and finish at the pavilion at Cady Way Park. The Marathon opens with a prologue that sets your total distance, then locks into 8 repeats. Every repeat is the same: a cul-de-sac near the tennis and pickleball courts, then out along the trail to a Forsyth Road turnaround. That's 16 bridge climbs. Every repeat crosses the SR 436 bridge: 685 feet of elevated asphalt rising over Semoran Blvd. It climbs. It descends. You come back to it every time. That is the point. Runners may access their own vehicle if parked along the course. Distances and Start Times 5:00 AM — Marathon and 50K 5:10 AM — Half Marathon 6:00 AM — 5K and 10K
Half Marathon - Day 1 (Saturday)
Half Marathon The 3-Day Bridge Challenge runs on Cady Way Trail in Winter Park, FL. Start and finish at the pavilion at Cady Way Park. The Half Marathon opens with a prologue that sets your total distance, then locks into 4 repeats. Every repeat is the same: a cul-de-sac near the tennis and pickleball courts, then out along the trail to a Forsyth Road turnaround. That's 8 bridge climbs. Every repeat crosses the SR 436 bridge: 685 feet of elevated asphalt rising over Semoran Blvd. It climbs. It descends. You come back to it every time. That is the point. Runners may access their own vehicle if parked along the course. Distances and Start Times 5:00 AM — Marathon and 50K 5:10 AM — Half Marathon 6:00 AM — 5K and 10K
10K - Day 1 (Saturday)
10K The 3-Day Bridge Challenge runs on Cady Way Trail in Winter Park, FL. Start and finish at the pavilion at Cady Way Park. The 10K opens with a prologue that sets your total distance, then locks into 2 repeats. Every repeat is the same: a cul-de-sac near the tennis and pickleball courts, then out along the trail to a Forsyth Road turnaround. That's 4 bridge climbs. Every repeat crosses the SR 436 bridge: 685 feet of elevated asphalt rising over Semoran Blvd. It climbs. It descends. You come back to it every time. That is the point. Runners may access their own vehicle if parked along the course. Distances and Start Times 5:00 AM — Marathon and 50K 5:10 AM — Half Marathon 6:00 AM — 5K and 10K
5K - Day 1 (Saturday)
5K The 3-Day Bridge Challenge runs on Cady Way Trail in Winter Park, FL. Start and finish at the pavilion at Cady Way Park. The 5K opens with a prologue that sets your total distance, then locks into 1 repeat: a cul-de-sac near the tennis and pickleball courts, then out along the trail to a Forsyth Road turnaround. That repeat crosses the SR 436 bridge twice — 685 feet of elevated asphalt rising over Semoran Blvd. It climbs. It descends. That is the point. Runners may access their own vehicle if parked along the course. Distances and Start Times 5:00 AM — Marathon and 50K 5:10 AM — Half Marathon 6:00 AM — 5K and 10K
Marathon - Day 2 (Sunday)
Marathon The 3-Day Bridge Challenge runs on Cady Way Trail in Winter Park, FL. Start and finish at the pavilion at Cady Way Park. The Marathon opens with a prologue that sets your total distance, then locks into 8 repeats. Every repeat is the same: a cul-de-sac near the tennis and pickleball courts, then out along the trail to a Forsyth Road turnaround. That's 16 bridge climbs. Every repeat crosses the SR 436 bridge: 685 feet of elevated asphalt rising over Semoran Blvd. It climbs. It descends. You come back to it every time. That is the point. Runners may access their own vehicle if parked along the course. Distances and Start Times 5:00 AM — Marathon and 50K 5:10 AM — Half Marathon 6:00 AM — 5K and 10K
Half Marathon - Day 2 (Sunday)
Half Marathon The 3-Day Bridge Challenge runs on Cady Way Trail in Winter Park, FL. Start and finish at the pavilion at Cady Way Park. The Half Marathon opens with a prologue that sets your total distance, then locks into 4 repeats. Every repeat is the same: a cul-de-sac near the tennis and pickleball courts, then out along the trail to a Forsyth Road turnaround. That's 8 bridge climbs. Every repeat crosses the SR 436 bridge: 685 feet of elevated asphalt rising over Semoran Blvd. It climbs. It descends. You come back to it every time. That is the point. Runners may access their own vehicle if parked along the course. Distances and Start Times 5:00 AM — Marathon and 50K 5:10 AM — Half Marathon 6:00 AM — 5K and 10K
10K - Day 2 (Sunday)
10K The 3-Day Bridge Challenge runs on Cady Way Trail in Winter Park, FL. Start and finish at the pavilion at Cady Way Park. The 10K opens with a prologue that sets your total distance, then locks into 2 repeats. Every repeat is the same: a cul-de-sac near the tennis and pickleball courts, then out along the trail to a Forsyth Road turnaround. That's 4 bridge climbs. Every repeat crosses the SR 436 bridge: 685 feet of elevated asphalt rising over Semoran Blvd. It climbs. It descends. You come back to it every time. That is the point. Runners may access their own vehicle if parked along the course. Distances and Start Times 5:00 AM — Marathon and 50K 5:10 AM — Half Marathon 6:00 AM — 5K and 10K
5K - Day 2 (Sunday)
5K The 3-Day Bridge Challenge runs on Cady Way Trail in Winter Park, FL. Start and finish at the pavilion at Cady Way Park. The 5K opens with a prologue that sets your total distance, then locks into 1 repeat: a cul-de-sac near the tennis and pickleball courts, then out along the trail to a Forsyth Road turnaround. That repeat crosses the SR 436 bridge twice — 685 feet of elevated asphalt rising over Semoran Blvd. It climbs. It descends. That is the point. Runners may access their own vehicle if parked along the course. Distances and Start Times 5:00 AM — Marathon and 50K 5:10 AM — Half Marathon 6:00 AM — 5K and 10K
Marathon - Day 3 (Monday)
Marathon The 3-Day Bridge Challenge runs on Cady Way Trail in Winter Park, FL. Start and finish at the pavilion at Cady Way Park. The Marathon opens with a prologue that sets your total distance, then locks into 8 repeats. Every repeat is the same: a cul-de-sac near the tennis and pickleball courts, then out along the trail to a Forsyth Road turnaround. That's 16 bridge climbs. Every repeat crosses the SR 436 bridge: 685 feet of elevated asphalt rising over Semoran Blvd. It climbs. It descends. You come back to it every time. That is the point. Runners may access their own vehicle if parked along the course. Distances and Start Times 5:00 AM — Marathon and 50K 5:10 AM — Half Marathon 6:00 AM — 5K and 10K
Half Marathon - Day 3 (Monday)
Half Marathon The 3-Day Bridge Challenge runs on Cady Way Trail in Winter Park, FL. Start and finish at the pavilion at Cady Way Park. The Half Marathon opens with a prologue that sets your total distance, then locks into 4 repeats. Every repeat is the same: a cul-de-sac near the tennis and pickleball courts, then out along the trail to a Forsyth Road turnaround. That's 8 bridge climbs. Every repeat crosses the SR 436 bridge: 685 feet of elevated asphalt rising over Semoran Blvd. It climbs. It descends. You come back to it every time. That is the point. Runners may access their own vehicle if parked along the course. Distances and Start Times 5:00 AM — Marathon and 50K 5:10 AM — Half Marathon 6:00 AM — 5K and 10K
10K - Day 3 (Monday)
10K The 3-Day Bridge Challenge runs on Cady Way Trail in Winter Park, FL. Start and finish at the pavilion at Cady Way Park. The 10K opens with a prologue that sets your total distance, then locks into 2 repeats. Every repeat is the same: a cul-de-sac near the tennis and pickleball courts, then out along the trail to a Forsyth Road turnaround. That's 4 bridge climbs. Every repeat crosses the SR 436 bridge: 685 feet of elevated asphalt rising over Semoran Blvd. It climbs. It descends. You come back to it every time. That is the point. Runners may access their own vehicle if parked along the course. Distances and Start Times 5:00 AM — Marathon and 50K 5:10 AM — Half Marathon 6:00 AM — 5K and 10K
5K - Day 3 (Monday)
5K The 3-Day Bridge Challenge runs on Cady Way Trail in Winter Park, FL. Start and finish at the pavilion at Cady Way Park. The 5K opens with a prologue that sets your total distance, then locks into 1 repeat: a cul-de-sac near the tennis and pickleball courts, then out along the trail to a Forsyth Road turnaround. That repeat crosses the SR 436 bridge twice — 685 feet of elevated asphalt rising over Semoran Blvd. It climbs. It descends. That is the point. Runners may access their own vehicle if parked along the course. Distances and Start Times 5:00 AM — Marathon and 50K 5:10 AM — Half Marathon 6:00 AM — 5K and 10K
Typical race-day weather
Based on 1 year of Open-Meteo archive data for this event's race dates in Winter Park, plus the 3 days either side.
The sun rises at 6:28 AM and sets at 8:17 PM local time (EDT) in Winter Park on May 29, 2027 — 13h 48m of daylight.
Course
No course map published yet.
The organizer hasn't released a route for this event, and we don't publish guesses. If you're the organizer, send us a GPX file and we'll draw the profile.
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🏃 Plan Your Next Race in Winter Park
Find upcoming events by distance:
- Winter Park 5K Races 7 races
- 10K Run Events in Winter Park 6 races
- Winter Park Half Marathons 6 races
- Marathons in Winter Park 6 races
- Winter Park Running Calendar 2026 7 races
Where this page comes from. Race details were last updated on . We re-check listings regularly and again in the week before race day.
- Entries, prices, waves and inclusions — the event's official registration page
- Temperature and humidity — Copernicus ERA5 reanalysis via Open-Meteo (CC BY 4.0)
- Elevation and terrain relief — Copernicus DEM GLO-90, ESA (CC BY 4.0)
- Comparisons and counts — Race Discovery calendar, 7 Winter Park events
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