Winter Park 50K, Marathon, Half, 10K & 5K – MileBuilt Cady Way Bridge 2-Day Challenge
From MileBuilt Endurance LLC
- 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, 10K & 5K – MileBuilt Cady Way Bridge 2-Day Challenge! Hosted by MileBuilt Endurance LLC, this exciting event takes place in the beautiful surroundings of Winter Park, Florida, from Saturday, February 20, 2027, to Sunday, February 21, 2027. Participants will traverse the picturesque Cady Way Trail, with race distances catering to all levels of runners, from the challenging 50K and Marathon to the more approachable Half Marathon, 10K, and 5K.
The unique format of this challenge means each day starts with a thrilling opening leg, followed by repeated laps that include a crossing over the impressive SR 436 bridge. Runners will enjoy a well-measured course and the camaraderie of fellow participants, all while aiming for their personal bests. Although this cupless event encourages participants to carry their own hydration, MileBuilt ensures water and snacks are provided at aid stations. Each finisher will receive a special Daily Finisher Medallion, and those daring enough to run both days will earn a coveted Tier Patch. Don't miss this chance to challenge yourself, make lasting
The unique format of this challenge means each day starts with a thrilling opening leg, followed by repeated laps that include a crossing over the impressive SR 436 bridge. Runners will enjoy a well-measured course and the camaraderie of fellow participants, all while aiming for their personal bests. Although this cupless event encourages participants to carry their own hydration, MileBuilt ensures water and snacks are provided at aid stations. Each finisher will receive a special Daily Finisher Medallion, and those daring enough to run both days will earn a coveted Tier Patch. Don't miss this chance to challenge yourself, make lasting
Organiser's Description
THE COURSE
The Cady Way Bridge 2-Day Challenge runs on the Cady Way Trail in Winter Park, FL, on FEBRUARY 2021, 2027. 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
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.
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, on FEBRUARY 2021, 2027. 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
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.
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 Course The Cady Way Bridge 2-Day Challenge runs on the Cady Way Trail in Winter Park, FL. Start and finish at the pavilion at Cady Way Park. The 50K starts with a one-time opening leg that sets your total distance, then runs 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. Every repeat crosses the SR 436 bridge: 685 feet of elevated asphalt rising over Semoran Blvd 20 bridge climbs in all. 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 -
Bridge 50K - Day 2
Incl. $6.10 Fee
Sun 21st February 2027 (5:00AM EST)
$91.10
50K The Course The Cady Way Bridge 2-Day Challenge runs on the Cady Way Trail in Winter Park, FL. Start and finish at the pavilion at Cady Way Park. The 50K starts with a one-time opening leg that sets your total distance, then runs 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. Every repeat crosses the SR 436 bridge: 685 feet of elevated asphalt rising over Semoran Blvd 20 bridge climbs in all. 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 -
Bridge Marathon - Day 1
Incl. $5.20 Fee
Sat 20th February 2027 (5:00AM EST)
$75.20
Marathon The Course The Cady Way Bridge 2-Day Challenge runs on the Cady Way Trail in Winter Park, FL. Start and finish at the pavilion at Cady Way Park. The Marathon starts with a one-time opening leg that sets your total distance, then runs 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. Every repeat crosses the SR 436 bridge: 685 feet of elevated asphalt rising over Semoran Blvd 16 bridge climbs in all. 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 -
Bridge Marathon - Day 2
Incl. $5.20 Fee
Sun 21st February 2027 (5:00AM EST)
$75.20
Marathon The Course The Cady Way Bridge 2-Day Challenge runs on the Cady Way Trail in Winter Park, FL. Start and finish at the pavilion at Cady Way Park. The Marathon starts with a one-time opening leg that sets your total distance, then runs 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. Every repeat crosses the SR 436 bridge: 685 feet of elevated asphalt rising over Semoran Blvd 16 bridge climbs in all. 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 -
Bridge Half Mar - Day 1
Incl. $4.60 Fee
Sat 20th February 2027 (5:10AM EST)
$64.60
Half Marathon The Course The Cady Way Bridge 2-Day Challenge runs on the Cady Way Trail in Winter Park, FL. Start and finish at the pavilion at Cady Way Park. The Half Marathon starts with a one-time opening leg that sets your total distance, then runs 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. Every repeat crosses the SR 436 bridge: 685 feet of elevated asphalt rising over Semoran Blvd 8 bridge climbs in all. 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 -
Bridge Half Mar - Day 2
Incl. $4.60 Fee
Sun 21st February 2027 (5:10AM EST)
$64.60
Half Marathon The Course The Cady Way Bridge 2-Day Challenge runs on the Cady Way Trail in Winter Park, FL. Start and finish at the pavilion at Cady Way Park. The Half Marathon starts with a one-time opening leg that sets your total distance, then runs 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. Every repeat crosses the SR 436 bridge: 685 feet of elevated asphalt rising over Semoran Blvd 8 bridge climbs in all. 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 -
Bridge 10K - Day 1
Incl. $3.70 Fee
Sat 20th February 2027 (6:00AM EST)
$48.70
10K The Course The Cady Way Bridge 2-Day Challenge runs on the Cady Way Trail in Winter Park, FL. Start and finish at the pavilion at Cady Way Park. The 10K starts with a one-time opening leg that sets your total distance, then runs 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. Every repeat crosses the SR 436 bridge: 685 feet of elevated asphalt rising over Semoran Blvd 4 bridge climbs in all. 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 -
Bridge 10K - Day 2
Incl. $3.70 Fee
Sun 21st February 2027 (6:00AM EST)
$48.70
10K The Course The Cady Way Bridge 2-Day Challenge runs on the Cady Way Trail in Winter Park, FL. Start and finish at the pavilion at Cady Way Park. The 10K starts with a one-time opening leg that sets your total distance, then runs 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. Every repeat crosses the SR 436 bridge: 685 feet of elevated asphalt rising over Semoran Blvd 4 bridge climbs in all. 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 -
Bridge 5K - Day 1
Incl. $3.10 Fee
Sat 20th February 2027 (6:00AM EST)
$38.10
5K The Course The Cady Way Bridge 2-Day Challenge runs on the Cady Way Trail in Winter Park, FL. Start and finish at the pavilion at Cady Way Park. The 5K starts with a one-time opening leg that sets your total distance, then runs 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 50K and Marathon 5:10 AM Half Marathon 6:00 AM 10K and 5K Available distances: 50K . Marathon . Half Marathon . 10K . 5K -
Bridge 5K - Day 2
Incl. $3.10 Fee
Sun 21st February 2027 (6:00AM EST)
$38.10
5K The Course The Cady Way Bridge 2-Day Challenge runs on the Cady Way Trail in Winter Park, FL. Start and finish at the pavilion at Cady Way Park. The 5K starts with a one-time opening leg that sets your total distance, then runs 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 50K and Marathon 5:10 AM Half Marathon 6:00 AM 10K and 5K Available distances: 50K . Marathon . Half Marathon . 10K . 5K
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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
