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Saturday
Bridge 50K - Day 1
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
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
Open to ages 18+.
- Distance Date:
- Saturday February 20, 2027
- Start Time:
- 5:00am EST
- End Time:
- 2:00pm EST
- Price:
- $85.00 Race Fee + $6.10 SignUp Fee
- Registration:
- Price increases to $95.00 after February 5, 2027 at 11:59pm EST
| Registration Starting | Registration Ending | Price |
|---|---|---|
| June 1, 2026, 7:00am EDT | February 5, 2027, 11:59pm EST | $85.00 Race Fee + $6.10 SignUp Fee |
| February 6, 2027, 12:00am EST | February 20, 2027, 6:00am EST | $95.00 Race Fee + $6.70 SignUp Fee |
Bridge Marathon - Day 1
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
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
Open to ages 18+.
- Distance Date:
- Saturday February 20, 2027
- Start Time:
- 5:00am EST
- End Time:
- 2:00pm EST
- Price:
- $70.00 Race Fee + $5.20 SignUp Fee
- Registration:
- Price increases to $80.00 after February 5, 2027 at 11:59pm EST
| Registration Starting | Registration Ending | Price |
|---|---|---|
| June 1, 2026, 7:00am EDT | February 5, 2027, 11:59pm EST | $70.00 Race Fee + $5.20 SignUp Fee |
| February 6, 2027, 12:00am EST | February 20, 2027, 6:00am EST | $80.00 Race Fee + $5.80 SignUp Fee |
Bridge Half Mar - Day 1
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
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
Open to ages 18+.
- Distance Date:
- Saturday February 20, 2027
- Start Time:
- 5:10am EST
- End Time:
- 2:00pm EST
- Price:
- $60.00 Race Fee + $4.60 SignUp Fee
- Registration:
- Price increases to $70.00 after February 5, 2027 at 11:59pm EST
| Registration Starting | Registration Ending | Price |
|---|---|---|
| June 1, 2026, 7:00am EDT | February 5, 2027, 11:59pm EST | $60.00 Race Fee + $4.60 SignUp Fee |
| February 6, 2027, 12:00am EST | February 20, 2027, 6:00am EST | $70.00 Race Fee + $5.20 SignUp Fee |
Bridge 10K - Day 1
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
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
Open to ages 18+.
- Distance Date:
- Saturday February 20, 2027
- Start Time:
- 6:00am EST
- End Time:
- 2:00pm EST
- Price:
- $45.00 Race Fee + $3.70 SignUp Fee
- Registration:
- Price increases to $50.00 after February 5, 2027 at 11:59pm EST
| Registration Starting | Registration Ending | Price |
|---|---|---|
| June 1, 2026, 7:00am EDT | February 5, 2027, 11:59pm EST | $45.00 Race Fee + $3.70 SignUp Fee |
| February 6, 2027, 12:00am EST | February 20, 2027, 7:00am EST | $50.00 Race Fee + $4.00 SignUp Fee |
Bridge 5K - Day 1
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
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
Open to ages 18+.
- Distance Date:
- Saturday February 20, 2027
- Start Time:
- 6:00am EST
- End Time:
- 2:00pm EST
- Price:
- $35.00 Race Fee + $3.10 SignUp Fee
- Registration:
- Price increases to $40.00 after February 5, 2027 at 11:59pm EST
| Registration Starting | Registration Ending | Price |
|---|---|---|
| June 1, 2026, 7:00am EDT | February 5, 2027, 11:59pm EST | $35.00 Race Fee + $3.10 SignUp Fee |
| February 6, 2027, 12:00am EST | February 20, 2027, 7:00am EST | $40.00 Race Fee + $3.40 SignUp Fee |
Sunday
Bridge 50K - Day 2
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
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
Open to ages 18+.
- Distance Date:
- Sunday February 21, 2027
- Start Time:
- 5:00am EST
- End Time:
- 2:00pm EST
- Price:
- $85.00 Race Fee + $6.10 SignUp Fee
- Registration:
- Price increases to $95.00 after February 6, 2027 at 11:59pm EST
| Registration Starting | Registration Ending | Price |
|---|---|---|
| July 4, 2026, 6:17pm EDT | February 6, 2027, 11:59pm EST | $85.00 Race Fee + $6.10 SignUp Fee |
| February 7, 2027, 12:00am EST | February 21, 2027, 6:00am EST | $95.00 Race Fee + $6.70 SignUp Fee |
Bridge Marathon - Day 2
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
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
Open to ages 18+.
- Distance Date:
- Sunday February 21, 2027
- Start Time:
- 5:00am EST
- End Time:
- 2:00pm EST
- Price:
- $70.00 Race Fee + $5.20 SignUp Fee
- Registration:
- Price increases to $80.00 after February 6, 2027 at 11:59pm EST
| Registration Starting | Registration Ending | Price |
|---|---|---|
| July 4, 2026, 6:17pm EDT | February 6, 2027, 11:59pm EST | $70.00 Race Fee + $5.20 SignUp Fee |
| February 7, 2027, 12:00am EST | February 21, 2027, 6:00am EST | $80.00 Race Fee + $5.80 SignUp Fee |
Bridge Half Mar - Day 2
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
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
Open to ages 18+.
- Distance Date:
- Sunday February 21, 2027
- Start Time:
- 5:10am EST
- End Time:
- 2:00pm EST
- Price:
- $60.00 Race Fee + $4.60 SignUp Fee
- Registration:
- Price increases to $70.00 after February 6, 2027 at 11:59pm EST
| Registration Starting | Registration Ending | Price |
|---|---|---|
| July 4, 2026, 6:17pm EDT | February 6, 2027, 11:59pm EST | $60.00 Race Fee + $4.60 SignUp Fee |
| February 7, 2027, 12:00am EST | February 21, 2027, 6:00am EST | $70.00 Race Fee + $5.20 SignUp Fee |
Bridge 10K - Day 2
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
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
Open to ages 18+.
- Distance Date:
- Sunday February 21, 2027
- Start Time:
- 6:00am EST
- End Time:
- 2:00pm EST
- Price:
- $45.00 Race Fee + $3.70 SignUp Fee
- Registration:
- Price increases to $50.00 after February 6, 2027 at 11:59pm EST
| Registration Starting | Registration Ending | Price |
|---|---|---|
| July 4, 2026, 6:17pm EDT | February 6, 2027, 11:59pm EST | $45.00 Race Fee + $3.70 SignUp Fee |
| February 7, 2027, 12:00am EST | February 21, 2027, 7:00am EST | $50.00 Race Fee + $4.00 SignUp Fee |
Bridge 5K - Day 2
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
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
Open to ages 18+.
- Distance Date:
- Sunday February 21, 2027
- Start Time:
- 6:00am EST
- End Time:
- 2:00pm EST
- Price:
- $35.00 Race Fee + $3.10 SignUp Fee
- Registration:
- Price increases to $40.00 after February 6, 2027 at 11:59pm EST
| Registration Starting | Registration Ending | Price |
|---|---|---|
| July 4, 2026, 6:17pm EDT | February 6, 2027, 11:59pm EST | $35.00 Race Fee + $3.10 SignUp Fee |
| February 7, 2027, 12:00am EST | February 21, 2027, 7:00am EST | $40.00 Race Fee + $3.40 SignUp Fee |
This is a service fee for processing your registration. This may be slightly higher or lower per registrant than the amount shown here.
