Winter Park 50K, Marathon, Half, 10K & 5K – MileBuilt Cady Way Bridge 2-Day Challenge
- Date Sat 20th February 2027 - Sun 21st February 2027
- Time 5:00AM EST
- Location Winter Park, Florida
- Price $38.10 - $91.10
- Races 10 races
- Distances Ultra, Marathon, Half Marathon, 10km, 5km
Event summary
Get ready for an exhilarating weekend of running at the Winter Park 50K, Marathon, Half Marathon, 10K, and 5K – the MileBuilt Cady Way Bridge 2-Day Challenge! Taking place from February 20th to 21st, 2027, in the beautiful setting of Winter Park, Orange, this event invites runners of all levels to experience the scenic Cady Way Trail. Each race distance begins with an exciting opening leg and includes multiple repeats of a unique course that features a thrilling 685-foot elevated asphalt bridge crossing over Semoran Blvd.
Participants can choose from five distances: the challenging 50K and Marathon starting at 5:00 AM, the Half Marathon at 5:10 AM, and the 10K and 5K at 6:00 AM. While this event emphasizes a straightforward approach with no frills—no shirts, no race bags, and no chip timing—every finisher receives a daily finisher medallion, and those who run both days earn a special tier patch for their commitment. Join fellow enthusiasts at Cady Way Park and embrace the spirit of camaraderie and competition during this unforgettable weekend of running!
Participants can choose from five distances: the challenging 50K and Marathon starting at 5:00 AM, the Half Marathon at 5:10 AM, and the 10K and 5K at 6:00 AM. While this event emphasizes a straightforward approach with no frills—no shirts, no race bags, and no chip timing—every finisher receives a daily finisher medallion, and those who run both days earn a special tier patch for their commitment. Join fellow enthusiasts at Cady Way Park and embrace the spirit of camaraderie and competition during this unforgettable weekend of running!
Organiser's Description
THE COURSE
The Cady Way Bridge 2-Day Challenge runs on the Cady Way Trail in Winter Park, FL. The course starts and finishes at the pavilion at Cady Way Park, 2535 Cady Way, Winter Park, FL 32792.
Every distance starts with a one-time opening leg that sets your total distance, then runs 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. 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 50K and Marathon
5:10 AM Half Marathon
6:00 AM 10K and 5K
Available distances: 50K . Marathon . Half Marathon . 10K . 5K
WHAT YOU GET. WHAT YOU DON'T.
No shirts. No race bags. No expo. No chip timing. Nothing in a bag at the finish.
A measured course. A clock. A finish that gets recorded. And a reason to come back tomorrow.
Every finisher earns the DAILY FINISHER MEDALLION. Run both days on a Streak and you earn the TIER PATCH.
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.
AGES
18 and older only every distance, every day. Volunteers must also be 18 or older.
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
This is a cupless event. Carry your own fluids handheld bottle, vest, or waist pack. MileBuilt provides water, an electrolyte drink, and basic snacks at the aid station. Do not rely on the aid station as your complete nutrition plan, especially for longer distances or multi-day participation.
BIB PICKUP
Bibs are available for pickup on race day beginning ONE HOUR BEFORE YOUR SCHEDULED START TIME honor system, no ID required. A friend may pick up your bib on your behalf. No bib transfers your bib is registered to you.
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.
ONE DAY IS A FULL RACE. TWO DAYS IS A STREAK.
The Cady Way Bridge 2-Day Challenge runs on the Cady Way Trail in Winter Park, FL. The course starts and finishes at the pavilion at Cady Way Park, 2535 Cady Way, Winter Park, FL 32792.
Every distance starts with a one-time opening leg that sets your total distance, then runs 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. 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 50K and Marathon
5:10 AM Half Marathon
6:00 AM 10K and 5K
Available distances: 50K . Marathon . Half Marathon . 10K . 5K
WHAT YOU GET. WHAT YOU DON'T.
No shirts. No race bags. No expo. No chip timing. Nothing in a bag at the finish.
A measured course. A clock. A finish that gets recorded. And a reason to come back tomorrow.
Every finisher earns the DAILY FINISHER MEDALLION. Run both days on a Streak and you earn the TIER PATCH.
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.
AGES
18 and older only every distance, every day. Volunteers must also be 18 or older.
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
This is a cupless event. Carry your own fluids handheld bottle, vest, or waist pack. MileBuilt provides water, an electrolyte drink, and basic snacks at the aid station. Do not rely on the aid station as your complete nutrition plan, especially for longer distances or multi-day participation.
BIB PICKUP
Bibs are available for pickup on race day beginning ONE HOUR BEFORE YOUR SCHEDULED START TIME honor system, no ID required. A friend may pick up your bib on your behalf. No bib transfers your bib is registered to you.
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.
ONE DAY IS A FULL RACE. TWO DAYS IS A STREAK.
Races
-
Bridge 50K - Day 1
Incl. $6.10 Fee
Sat 20th February 2027 (5:00AM EST)
$91.10
50K The 2-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 -
Bridge 50K - Day 2
Incl. $6.10 Fee
Sun 21st February 2027 (5:00AM EST)
$91.10
50K The 2-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 -
Bridge Marathon - Day 1
Incl. $5.20 Fee
Sat 20th February 2027 (5:00AM EST)
$75.20
Marathon The 2-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 -
Bridge Marathon - Day 2
Incl. $5.20 Fee
Sun 21st February 2027 (5:00AM EST)
$75.20
Marathon The 2-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 -
Bridge Half Mar - Day 1
Incl. $4.60 Fee
Sat 20th February 2027 (5:10AM EST)
$64.60
Half Marathon The 2-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 -
Bridge Half Mar - Day 2
Incl. $4.60 Fee
Sun 21st February 2027 (5:10AM EST)
$64.60
Half Marathon The 2-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 -
Bridge 10K - Day 1
Incl. $3.70 Fee
Sat 20th February 2027 (6:00AM EST)
$48.70
10K The 2-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 -
Bridge 10K - Day 2
Incl. $3.70 Fee
Sun 21st February 2027 (6:00AM EST)
$48.70
10K The 2-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 -
Bridge 5K - Day 1
Incl. $3.10 Fee
Sat 20th February 2027 (6:00AM EST)
$38.10
5K The 2-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 -
Bridge 5K - Day 2
Incl. $3.10 Fee
Sun 21st February 2027 (6:00AM EST)
$38.10
5K The 2-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
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Location
2535 Cady Way, Winter Park, 32792, FL, United States
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Winter Park 50K, Marathon, Half, 10K & 5K – MileBuilt Cady Way Bridge 2-Day Challenge
