MileBuilt 2-Day Bridge Challenge
About this race
THE RACE
The 2-Day Bridge Challenge runs on the Cady Way Trail in Winter Park, FL on February 20–21, 2027. This is a modified out-and-back on an accessible, measured trail. Pick your distance. Pick your path. Show up and run.
THE COURSE
The race starts and finishes at the pavilion at Cady Way Park. Every repeat brings you back to the SR 436 bridge — 685 feet of elevated asphalt rising over Semoran Blvd. It climbs. It descends. And you come back to it. Every repeat. It does not get easier. It gets familiar. There is no way around it. That is the point. Runners may access their own vehicle if parked along the course.
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
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.
TWO WAYS TO REGISTER
Standalone — one race day, one distance. No pledge. No tier. Daily finisher recognition.
2-Day Streak — both days, consecutive. Sign your personal pledge. Earn built-in Streak pricing and your tier patch upon completion.
To register as a Streak runner, select 2-Day Streak at registration — not the individual day listings. You will pick your distance for Day 1 and Day 2 and sign your personal pledge before checkout. Registering for each day separately puts you in as Standalone. The Streak path is its own registration option.
THIS IS A BARE-BONES EVENT
No shirts. No race bags. No expo. No chip timing. No disposable cups. You carry your own hydration — handheld bottle, vest, or waist pack. Water, electrolytes, and basic snacks are at the aid station. The rest is on you.
Timing is manual. When you finish: cross the line, strike the GONG, pull your Finish Ticket, and record your bib number, ticket number, distance, and race clock time in the Finish Ledger. Times are posted in hour and minute format only. No ledger entry = no official finish record.
COURSE SUPPORT
Start and finish line only. Runners may access their own vehicle if parked along the course.
BIBS
Bibs available for pickup on race day beginning one hour before your scheduled start time. No ID required. A friend may pick up on your behalf. No bib transfers.
HEADPHONES
Use of personal audio devices is strongly discouraged. Be aware of your surroundings at all times.
Join fellow runners on February 20, 2027 for the MileBuilt 2-Day Bridge Challenge. It's a fantastic Ultra, Marathon, Half-Marathon, 10K, 5K featuring a flat and fast course in Winter Park.
Pick your distance
Trail running
50K - Day 1 (Saturday)
The Course The 2-Day Bridge Challenge runs on Cady Way Trail in Winter Park, FL. The course starts and finishes at the pavilion at Cady Way Park. Every distance follows the same modified out-and-back route — 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 — Marathon and 50K 5:10 AM — Half Marathon 6:00 AM — 5K and 10K Available distances: 5K · 10K · Half Marathon · Marathon · 50K Parking Cady Way Park. Use the central lot or the overflow lot across from the pool — both open early. The cul-de-sac and pool lots fill later. Arrive early. Race Day Cutoff 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. 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 MileBuilt uses the Finish Ticket system — not chip timing. When you finish: cross the line, strike the GONG, pull your MileBuilt Finish Ticket, and record your bib number, ticket number, distance, and race clock time in the Finish Ledger. Times are posted in hour and minute format only. Seconds are not recorded or posted. If you do not record in the Finish Ledger, you will have no official finish record.
50K - Day 2 (Sunday)
The Course The 2-Day Bridge Challenge runs on Cady Way Trail in Winter Park, FL. The course starts and finishes at the pavilion at Cady Way Park. Every distance follows the same modified out-and-back route — 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 — Marathon and 50K 5:10 AM — Half Marathon 6:00 AM — 5K and 10K Available distances: 5K · 10K · Half Marathon · Marathon · 50K Parking Cady Way Park. Use the central lot or the overflow lot across from the pool — both open early. The cul-de-sac and pool lots fill later. Arrive early. Race Day Cutoff 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. 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 MileBuilt uses the Finish Ticket system — not chip timing. When you finish: cross the line, strike the GONG, pull your MileBuilt Finish Ticket, and record your bib number, ticket number, distance, and race clock time in the Finish Ledger. Times are posted in hour and minute format only. Seconds are not recorded or posted. If you do not record in the Finish Ledger, you will have no official finish record.
Running
Marathon - Day 1 (Saturday)
The Course The 2-Day Bridge Challenge runs on Cady Way Trail in Winter Park, FL. The course starts and finishes at the pavilion at Cady Way Park. Every distance follows the same modified out-and-back route — 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 — Marathon and 50K 5:10 AM — Half Marathon 6:00 AM — 5K and 10K Available distances: 5K · 10K · Half Marathon · Marathon · 50K Parking Cady Way Park. Use the central lot or the overflow lot across from the pool — both open early. The cul-de-sac and pool lots fill later. Arrive early. Race Day Cutoff 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. 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 MileBuilt uses the Finish Ticket system — not chip timing. When you finish: cross the line, strike the GONG, pull your MileBuilt Finish Ticket, and record your bib number, ticket number, distance, and race clock time in the Finish Ledger. Times are posted in hour and minute format only. Seconds are not recorded or posted. If you do not record in the Finish Ledger, you will have no official finish record.
Half Marathon - Day 1 (Saturday)
The Course The 2-Day Bridge Challenge runs on Cady Way Trail in Winter Park, FL. The course starts and finishes at the pavilion at Cady Way Park. Every distance follows the same modified out-and-back route — 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 — Marathon and 50K 5:10 AM — Half Marathon 6:00 AM — 5K and 10K Available distances: 5K · 10K · Half Marathon · Marathon · 50K Parking Cady Way Park. Use the central lot or the overflow lot across from the pool — both open early. The cul-de-sac and pool lots fill later. Arrive early. Race Day Cutoff 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. 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 MileBuilt uses the Finish Ticket system — not chip timing. When you finish: cross the line, strike the GONG, pull your MileBuilt Finish Ticket, and record your bib number, ticket number, distance, and race clock time in the Finish Ledger. Times are posted in hour and minute format only. Seconds are not recorded or posted. If you do not record in the Finish Ledger, you will have no official finish record.
10K - Day 1 (Saturday)
The Course The 2-Day Bridge Challenge runs on Cady Way Trail in Winter Park, FL. The course starts and finishes at the pavilion at Cady Way Park. Every distance follows the same modified out-and-back route — 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 — Marathon and 50K 5:10 AM — Half Marathon 6:00 AM — 5K and 10K Available distances: 5K · 10K · Half Marathon · Marathon · 50K Parking Cady Way Park. Use the central lot or the overflow lot across from the pool — both open early. The cul-de-sac and pool lots fill later. Arrive early. Race Day Cutoff 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. 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 MileBuilt uses the Finish Ticket system — not chip timing. When you finish: cross the line, strike the GONG, pull your MileBuilt Finish Ticket, and record your bib number, ticket number, distance, and race clock time in the Finish Ledger. Times are posted in hour and minute format only. Seconds are not recorded or posted. If you do not record in the Finish Ledger, you will have no official finish record.
5K - Day 1 (Saturday)
The Course The 2-Day Bridge Challenge runs on Cady Way Trail in Winter Park, FL. The course starts and finishes at the pavilion at Cady Way Park. Every distance follows the same modified out-and-back route — 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 — Marathon and 50K 5:10 AM — Half Marathon 6:00 AM — 5K and 10K Available distances: 5K · 10K · Half Marathon · Marathon · 50K Parking Cady Way Park. Use the central lot or the overflow lot across from the pool — both open early. The cul-de-sac and pool lots fill later. Arrive early. Race Day Cutoff 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. 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 MileBuilt uses the Finish Ticket system — not chip timing. When you finish: cross the line, strike the GONG, pull your MileBuilt Finish Ticket, and record your bib number, ticket number, distance, and race clock time in the Finish Ledger. Times are posted in hour and minute format only. Seconds are not recorded or posted. If you do not record in the Finish Ledger, you will have no official finish record.
Marathon - Day 2 (Sunday)
The Course The 2-Day Bridge Challenge runs on Cady Way Trail in Winter Park, FL. The course starts and finishes at the pavilion at Cady Way Park. Every distance follows the same modified out-and-back route — 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 — Marathon and 50K 5:10 AM — Half Marathon 6:00 AM — 5K and 10K Available distances: 5K · 10K · Half Marathon · Marathon · 50K Parking Cady Way Park. Use the central lot or the overflow lot across from the pool — both open early. The cul-de-sac and pool lots fill later. Arrive early. Race Day Cutoff 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. 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 MileBuilt uses the Finish Ticket system — not chip timing. When you finish: cross the line, strike the GONG, pull your MileBuilt Finish Ticket, and record your bib number, ticket number, distance, and race clock time in the Finish Ledger. Times are posted in hour and minute format only. Seconds are not recorded or posted. If you do not record in the Finish Ledger, you will have no official finish record.
Half Marathon - Day 2 (Sunday)
The Course The 2-Day Bridge Challenge runs on Cady Way Trail in Winter Park, FL. The course starts and finishes at the pavilion at Cady Way Park. Every distance follows the same modified out-and-back route — 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 — Marathon and 50K 5:10 AM — Half Marathon 6:00 AM — 5K and 10K Available distances: 5K · 10K · Half Marathon · Marathon · 50K Parking Cady Way Park. Use the central lot or the overflow lot across from the pool — both open early. The cul-de-sac and pool lots fill later. Arrive early. Race Day Cutoff 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. 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 MileBuilt uses the Finish Ticket system — not chip timing. When you finish: cross the line, strike the GONG, pull your MileBuilt Finish Ticket, and record your bib number, ticket number, distance, and race clock time in the Finish Ledger. Times are posted in hour and minute format only. Seconds are not recorded or posted. If you do not record in the Finish Ledger, you will have no official finish record.
10K - Day 2 (Sunday)
The Course The 2-Day Bridge Challenge runs on Cady Way Trail in Winter Park, FL. The course starts and finishes at the pavilion at Cady Way Park. Every distance follows the same modified out-and-back route — 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 — Marathon and 50K 5:10 AM — Half Marathon 6:00 AM — 5K and 10K Available distances: 5K · 10K · Half Marathon · Marathon · 50K Parking Cady Way Park. Use the central lot or the overflow lot across from the pool — both open early. The cul-de-sac and pool lots fill later. Arrive early. Race Day Cutoff 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. 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 MileBuilt uses the Finish Ticket system — not chip timing. When you finish: cross the line, strike the GONG, pull your MileBuilt Finish Ticket, and record your bib number, ticket number, distance, and race clock time in the Finish Ledger. Times are posted in hour and minute format only. Seconds are not recorded or posted. If you do not record in the Finish Ledger, you will have no official finish record.
5K - Day 2 (Sunday)
The Course The 2-Day Bridge Challenge runs on Cady Way Trail in Winter Park, FL. The course starts and finishes at the pavilion at Cady Way Park. Every distance follows the same modified out-and-back route — 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 — Marathon and 50K 5:10 AM — Half Marathon 6:00 AM — 5K and 10K Available distances: 5K · 10K · Half Marathon · Marathon · 50K Parking Cady Way Park. Use the central lot or the overflow lot across from the pool — both open early. The cul-de-sac and pool lots fill later. Arrive early. Race Day Cutoff 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. 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 MileBuilt uses the Finish Ticket system — not chip timing. When you finish: cross the line, strike the GONG, pull your MileBuilt Finish Ticket, and record your bib number, ticket number, distance, and race clock time in the Finish Ledger. Times are posted in hour and minute format only. Seconds are not recorded or posted. If you do not record in the Finish Ledger, you will have no official finish record.
About Winter Park
MileBuilt 2-Day Bridge Challenge takes place in Winter Park, Florida, United States. The local timezone is America/New_York.
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Race information has been sourced from the event's official website and other publicly available resources. For the most up-to-date details, please refer to the official website directly. If you notice any incorrect or missing information, don't hesitate to reach out to us by email.
