Saturday and Sunday, February 20–21, 2027, at Cady Way Park in Winter Park, FL.
Race day cutoff: 2:00 PM
Race day cutoff: 2:00 PM
Each race day is its own race, with its own official finish record. Run one day as a Standalone, or run both days as a Streak. See All Race Days →
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 opens with a prologue that sets your total distance, then locks into 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.
Runners may access their own vehicle if parked along the course.
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.
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.
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.
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.
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.
Every finish earns the Daily Finisher Medallion. Run every day on a Streak and you earn the Tier Patch.
One race day. Pick any distance. No pledge. No tier. Daily Finisher Medallion.
Every day, consecutive. Sign your personal pledge at registration. Built-in Streak pricing. Earn your Tier Patch upon completion.
Volunteer shifts for the Cady Way Bridge 2-Day Challenge are live on RunSignup. Friends and family supporting a runner are welcome. Volunteers may earn race credit toward future MileBuilt races based on verified hours.
Register on RunSignup. Prices are shown at registration — not on this website.