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

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

MileBuilt 2-Day Bridge Challenge: a bare-bones multi-day half marathon on a measured trail.

Race Date

Feb 20, 2027

Location

Winter Park, FL

Quick facts

Date
Saturday, February 20, 2027
Location
Winter Park, Florida
Distance
Half marathon (13.1 mi)
Course
Out & Back
Terrain
Road
USATF certified
Not listed

Highlights

Atmosphere

Low KeyLocal CommunityBare BonesEasy Parking

The Experience

The MileBuilt 2-Day Bridge Challenge unfolds along the Cady Way Trail in Winter Park, Florida, a measured multi-use path that becomes a test of discipline and consistency. This no-frills event strips racing to its essentials: no shirts, no race bags, no chip timing. Runners start in the early morning from Cady Way Park, following a modified out-and-back route that repeatedly brings them to the SR 436 bridge — 685 feet of elevated asphalt over Semoran Boulevard. The bridge does not get easier, the organizers warn; it gets familiar. That is the challenge and the reward.

The half marathon is run on one of the five distances offered, and core distances are repeated on both Saturday and Sunday, making this a true multi-day endurance challenge. The atmosphere is low-key and self-sufficient: runners carry their own fluids in a cupless event, crossing the finish line and striking a gong. Without the fanfare of a large production, the race attracts a grassroots community of runners who value perseverance over fluff. Parking is easy at the park, and the pre-race bib pickup runs on the honor system. For those seeking a stripped-down, focused racing experience, the Bridge Challenge delivers.

Race-provided description

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.

Logistics

Race Day

Saturday, February 20, 2027

Start Time

5:10 AM

Start Location

2535 Cady Way, Winter Park, FL, 32792

Directions

Course Info

Course Type

Out & Back

Terrain

road

Surface

Paved

Difficulty

Ultra-Flat

Quality Score

Methodology
Heritage0/20

first year

Size0/15

no finisher counts yet

Momentum3/5

small race — neutral

Loyalty0/20

needs a few years of results

Course & details0/15

limited extras

National draw0/10

no finisher data yet

Front-pack speed0/5

no winner time yet

Weather2/10

typical high 75°F

Race Day Weather

5-year historical avg

Start (Low)

55°

Afternoon (High)

75°

Warm — hydration strategy is key, start conservatively

0.1"

Precipitation

11 mph

Wind

75%

Humidity

Frequently asked

When is the Winter Park 50K, Marathon, Half, 10K & 5K – MileBuilt Cady Way Bridge 2-Day Challenge?

The Winter Park 50K, Marathon, Half, 10K & 5K – MileBuilt Cady Way Bridge 2-Day Challenge is held on Saturday, February 20, 2027, starting at 5:10 AM.

Where does the Winter Park 50K, Marathon, Half, 10K & 5K – MileBuilt Cady Way Bridge 2-Day Challenge take place?

It takes place in Winter Park, Florida.

What distances does the Winter Park 50K, Marathon, Half, 10K & 5K – MileBuilt Cady Way Bridge 2-Day Challenge offer?

The half marathon (13.1 miles).

Is the Winter Park 50K, Marathon, Half, 10K & 5K – MileBuilt Cady Way Bridge 2-Day Challenge course flat and good for a PR?

The Winter Park 50K, Marathon, Half, 10K & 5K – MileBuilt Cady Way Bridge 2-Day Challenge is a ultra-flat, out & back course.

HalfRuns editorial — independent, no paid placement.

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