Winter Park 50K, Marathon, Half, 10K & 5K – MileBuilt Cady Way Bridge Memorial Day 3-Day Challenge
- Date Sat 29th May 2027 - Mon 31st May 2027
- Time 5:00AM EDT
- Location Winter Park, Florida
- Price $38.10 - $91.10
- Races 15 races
- Distances Ultra, Marathon, Half Marathon, 10km, 5km
Event summary
Get ready for an exciting weekend of running at the Winter Park 50K, Marathon, Half, 10K & 5K – MileBuilt Cady Way Bridge Memorial Day 3-Day Challenge, taking place from May 29 to May 31, 2027, in the picturesque Winter Park, Florida. This unique event invites runners of all skill levels to tackle a variety of distances, including a challenging 50K, a full marathon, a half marathon, a 10K, and a 5K.
Runners will enjoy the scenic Cady Way Trail, starting and finishing at the pavilion in Cady Way Park. Each race distance features a thrilling loop that includes a climb up the SR 436 bridge, offering stunning views and an exhilarating experience. Participants have the opportunity to earn a DAILY FINISHER MEDALLION, and those who complete all three days will receive a coveted TIER PATCH. Note that this is a cupless event, encouraging runners to carry their own fluids, and the atmosphere is all about camaraderie and personal achievement. Whether you’re there for the thrill of competition or the joy of running, the Winter Park 3-Day Challenge promises to be an unforgettable experience for all!
Runners will enjoy the scenic Cady Way Trail, starting and finishing at the pavilion in Cady Way Park. Each race distance features a thrilling loop that includes a climb up the SR 436 bridge, offering stunning views and an exhilarating experience. Participants have the opportunity to earn a DAILY FINISHER MEDALLION, and those who complete all three days will receive a coveted TIER PATCH. Note that this is a cupless event, encouraging runners to carry their own fluids, and the atmosphere is all about camaraderie and personal achievement. Whether you’re there for the thrill of competition or the joy of running, the Winter Park 3-Day Challenge promises to be an unforgettable experience for all!
Organiser's Description
THE COURSE
The Cady Way Bridge Memorial Day 3-Day Challenge runs on the Cady Way Trail in Winter Park, FL, on MAY 2931, 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 all three 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 RESOLVE. THREE DAYS IS A STREAK.
The Cady Way Bridge Memorial Day 3-Day Challenge runs on the Cady Way Trail in Winter Park, FL, on MAY 2931, 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 all three 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 RESOLVE. THREE DAYS IS A STREAK.
Races
-
Memorial Bridge 50K - Day 1
Incl. $6.10 Fee
Sat 29th May 2027 (5:00AM EDT)
$91.10
50K The Course The Cady Way Bridge Memorial Day 3-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 -
Memorial Bridge 50K - Day 2
Incl. $6.10 Fee
Sun 30th May 2027 (5:00AM EDT)
$91.10
50K The Course The Cady Way Bridge Memorial Day 3-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 -
Memorial Bridge 50K - Day 3
Incl. $6.10 Fee
Mon 31st May 2027 (5:00AM EDT)
$91.10
50K The Course The Cady Way Bridge Memorial Day 3-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 -
Memorial Bridge Marathon - Day 1
Incl. $5.20 Fee
Sat 29th May 2027 (5:00AM EDT)
$75.20
Marathon The Course The Cady Way Bridge Memorial Day 3-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 -
Memorial Bridge Marathon - Day 2
Incl. $5.20 Fee
Sun 30th May 2027 (5:00AM EDT)
$75.20
Marathon The Course The Cady Way Bridge Memorial Day 3-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 -
Memorial Bridge Marathon - Day 3
Incl. $5.20 Fee
Mon 31st May 2027 (5:00AM EDT)
$75.20
Marathon The Course The Cady Way Bridge Memorial Day 3-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 -
Memorial Bridge Half Marathon - Day 1
Incl. $4.60 Fee
Sat 29th May 2027 (5:10AM EDT)
$64.60
Half Marathon The Course The Cady Way Bridge Memorial Day 3-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 -
Memorial Bridge Half Marathon - Day 2
Incl. $4.60 Fee
Sun 30th May 2027 (5:10AM EDT)
$64.60
Half Marathon The Course The Cady Way Bridge Memorial Day 3-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 -
Memorial Bridge Half Marathon - Day 3
Incl. $4.60 Fee
Mon 31st May 2027 (5:10AM EDT)
$64.60
Half Marathon The Course The Cady Way Bridge Memorial Day 3-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 -
Memorial Bridge 10K - Day 1
Incl. $3.70 Fee
Sat 29th May 2027 (6:00AM EDT)
$48.70
10K The Course The Cady Way Bridge Memorial Day 3-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 -
Memorial Bridge 10K - Day 2
Incl. $3.70 Fee
Sun 30th May 2027 (6:00AM EDT)
$48.70
10K The Course The Cady Way Bridge Memorial Day 3-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 -
Memorial Bridge 10K - Day 3
Incl. $3.70 Fee
Mon 31st May 2027 (6:00AM EDT)
$48.70
10K The Course The Cady Way Bridge Memorial Day 3-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 -
Memorial Bridge 5K - Day 1
Incl. $3.10 Fee
Sat 29th May 2027 (6:00AM EDT)
$38.10
5K The Course The Cady Way Bridge Memorial Day 3-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 -
Memorial Bridge 5K - Day 2
Incl. $3.10 Fee
Sun 30th May 2027 (6:00AM EDT)
$38.10
5K The Course The Cady Way Bridge Memorial Day 3-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 -
Memorial Bridge 5K - Day 3
Incl. $3.10 Fee
Mon 31st May 2027 (6:00AM EDT)
$38.10
5K The Course The Cady Way Bridge Memorial Day 3-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
Reviews
Doing this event?
First-hand event reviews from people who have been there, done that and got the breathable T-shirt, really help everyone choose their next event. You'll be able to review this event once it's taken place.
Location
2535 Cady Way, Winter Park, 32792, FL, United States
Who's In
See who else is doing this event
Be the first
No-one has marked this event as 'Doing' or 'Maybe' yet. Will you be the first?
Winter Park 50K, Marathon, Half, 10K & 5K – MileBuilt Cady Way Bridge Memorial Day 3-Day Challenge
