THE RACE The 2-Day Bridge Challenge runs on Cady Way Trail in Winter Park, FL on February 20–21, 2027. A modified out-and-back on an accessible, measured trail. Every distance opens with a prologue, then locks into repeats. Every repeat brings you back to the SR 436 bridge — 685 feet of elevated asphalt over Semoran Blvd. It does not get easier. It gets familiar. That is the point. Five distances: 5K · 10K · Half Marathon · Marathon · 50K. Core distances run both days. 50K is confirmed for this event. START TIMES 5:00 AM — Marathon and 50K 5:10 AM — Half Marathon 6:00 AM — 5K and 10K 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. 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 Cupless event. Carry your own fluids — handheld bottle, vest, or waist pack. MileBuilt provides water, an electrolyte drink, and basic snacks. 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. BARE-BONES EVENT No shirts. No race bags. No expo. 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.
Course & Travel Notes
Plan for mild but cool conditions in late February at Winter Park, with typical highs around 74°F and lows near 54°F, so bring layers for the early 5:00 AM start before sunrise at 6:59 AM; rain gear is worth considering since about 27% of days see measurable precipitation this time of year. The venue sits at just 95 feet elevation, so altitude adjustment won't be a concern. Orlando Executive Airport is conveniently located just 3.4 miles from the race, making it easy to arrange ground transportation to the venue.
⛰️ 95 ft elevation☀️ Typically 74°F / 54°F · 27% chance of rain✈️ Orlando Executive Airport (ORL) — 3.4 mi
Hotels Near This Race
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MileBuilt 2-Day Bridge Challenge 2027 — Winter Park, FL
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Race Travel Insurance
Don't forget travel insurance for February 20.
You've trained for months and booked a trip to Winter Park, FL.
A pre-race injury, a delayed flight, or a family emergency can derail the whole thing.
Travel insurance can help cover your race entry fee, hotel, and flights if you can't make it,
and may cover medical costs if something goes wrong on the course. Plans typically only run
5-7% of your total trip cost — and running events are covered under standard plans with no
additional coverage needed.
Trip cancellation up to 100% of prepaid costs
Running events covered under standard plans — no add-ons needed
Trip interruption up to 150% of non-refundable costs
When is MileBuilt 2-Day Bridge Challenge 2027 — Winter Park, FL?
MileBuilt 2-Day Bridge Challenge 2027 — Winter Park, FL takes place on February 20, 2027. The race is held in Winter Park, Florida.
Where is MileBuilt 2-Day Bridge Challenge 2027 — Winter Park, FL held?
MileBuilt 2-Day Bridge Challenge 2027 — Winter Park, FL is held at 2535 Cady Way in Winter Park, Florida.
Where can I find hotels near MileBuilt 2-Day Bridge Challenge 2027 — Winter Park, FL?
RaceHotelFinder shows hotels sorted by distance from the race venue in Winter Park. Use the map or list view on this page to compare options and book race weekend accommodation.
