In 111 days · Sat, Feb 20, 2027
Don't let race day sneak up
One email during race week. That's it.
Saturday, February 20th, 2027
2535 Cady Way, Winter Park FL
Ultra · Marathon · Half · 10K
58–77°F · low rain risk
See last 10 years
On this date: rain 1 of the last 10 years
2026
64–88°F
dry
2025
53–65°F
dry
2024
42–66°F
dry
2023
58–83°F
dry
2022
52–74°F
dry
2021
48–63°F
dry
2020
67–81°F
rain
2019
69–81°F
dry
2018
68–86°F
dry
2017
57–80°F
dry
Best months to race in Florida →
About this race
THE COURSE
The Cady Way Bridge 2-Day Challenge runs on the Cady Way Trail in Winter Park, FL, on February 20–21, 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.
Course map
Train with a club
Run clubs near Winter Park to train with before race day.
Suggested Races
Organize this race?
Claim it free to manage your listing — and get it featured for free, while spots last.