
Winter Park 50K, Marathon, Half, 10K & 5K – MileBuilt Cady Way Bridge 2-Day Challenge
About This Event
THE COURSE The Cady Way Bridge 2-Day Challenge runs on the Cady Way Trail in Winter Park, FL. 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 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 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.
Race Distances
Ready to run?
Registration Pricing
Bridge 50K - Day 1
$85.00
+ $6.10 processing fee
event_busy Goes up to $95.00 after Feb 5, 2027
Bridge 50K - Day 2
$85.00
+ $6.10 processing fee
event_busy Goes up to $95.00 after Feb 6, 2027
Bridge Marathon - Day 1
$70.00
+ $5.20 processing fee
event_busy Goes up to $80.00 after Feb 5, 2027
Bridge Marathon - Day 2
$70.00
+ $5.20 processing fee
event_busy Goes up to $80.00 after Feb 6, 2027
Bridge Half Mar - Day 1
$60.00
+ $4.60 processing fee
event_busy Goes up to $70.00 after Feb 5, 2027
Bridge Half Mar - Day 2
$60.00
+ $4.60 processing fee
event_busy Goes up to $70.00 after Feb 6, 2027
Bridge 10K - Day 1
$45.00
+ $3.70 processing fee
event_busy Goes up to $50.00 after Feb 5, 2027
Bridge 10K - Day 2
$45.00
+ $3.70 processing fee
event_busy Goes up to $50.00 after Feb 6, 2027
Bridge 5K - Day 1
$35.00
+ $3.10 processing fee
event_busy Goes up to $40.00 after Feb 5, 2027
Bridge 5K - Day 2
$35.00
+ $3.10 processing fee
event_busy Goes up to $40.00 after Feb 6, 2027
Prices from the official registration page, updated several times a day.
Registration links may earn us a small commission at no extra cost to you.
Weather
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Race Day Schedule
2/20/2027 05:00
50K Start
2/21/2027 05:00
50K Start
2/20/2027 05:00
Marathon Start
2/21/2027 05:10
Half Marathon Start
2/20/2027 06:00
10K Start
2/21/2027 06:00
10K Start
2/20/2027 06:00
5K Start
2/21/2027 06:00
5K Start
2/21/2027 05:00
Marathon Start
2/20/2027 05:10
Half Marathon Start
Registration
Registration links may earn us a small commission at no extra cost to you.
Local Running Stores
Clermont, Central Florida
Dash Sports is Clermont's specialty running and walking shoe store, serving the South Lake County running community from its location on West Montrose Street in downtown Clermont. The store takes a thorough approach to fitting — each customer receives a custom gait and foot analysis that typically runs 20 to 40 minutes, ensuring the shoe recommendation is grounded in how you actually move. Clermont's reputation as a triathlon and endurance sports hub makes Dash Sports a natural resource for serious athletes alongside everyday runners and walkers. The store carries a strong lineup of performance brands including Hoka, On Running, Brooks, New Balance, and Altra, giving customers access to the leading options in road, trail, and stability footwear. Dash Sports also stocks Olukai and Aetrex for customers seeking comfort and orthopedic options alongside performance footwear — rounding out a selection that serves runners, walkers, and recovery-focused athletes alike.
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Fit2Run at Disney Springs is the only running specialty store inside the Walt Disney World Resort destination. Open late to serve resort guests and locals alike, offering gait analysis, top performance brands, and a one-of-a-kind running store experience in the heart of Central Florida tourism.
phone (407) 743-5990 language Visit WebsiteRunner's gear
Gear for race day

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Winter Park 50K, Marathon, Half, 10K & 5K – MileBuilt Cady Way Bridge 2-Day Challenge
February 20, 2027