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

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 is a running and ultra race on February 20–21, 2027 in Winter Park, FL, with entry fees from $35 to $85.

Date
February 20–21, 2027 (132 days to go)
Price
$35–$85
Sports
RunningUltra

From the Organizer

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.

Events

Marathon - Day 1 (Saturday)$70
50K - Day 1 (Saturday)$85
Half Marathon - Day 1 (Saturday)$60
5K - Day 1 (Saturday)$35
10K - Day 1 (Saturday)$45
Marathon - Day 2 (Sunday)$70
50K - Day 2 (Sunday)$85
Half Marathon - Day 2 (Sunday)$60
5K - Day 2 (Sunday)$35
10K - Day 2 (Sunday)$45

Typical Conditions

It's too far out for a forecast, so here's what weather on this date is normally like in the area. A race day forecast will replace this as race week approaches.

Typical High

75°

Typical Low

55°

Chance of Rain

25%

Based on US Climate Normals data from Orlando Executive Ap, 3 mi from the venue.

Sunrise 6:59 AMSunset 6:19 PMDaylight 11h 20m

About Winter Park, FL

City Elevation

88 ft

Nearest Airport

MCO

Orlando International Airport · 11 mi

Time Zone

Eastern Time

From Endurance Grid

Line up lodging and travel early to lock in your race weekend.

Race Location

What Are You
Waiting For?

Every finish line starts with a single decision. Claim your spot at Winter Park 50K, Marathon, Half, 10K & 5K – MileBuilt Cady Way Bridge 2-Day Challenge, put it on the calendar, and turn “someday” into a start date.

132

Days to train

Race
Winter Park 50K, Marathon, Half, 10K & 5K – MileBuilt Cady Way Bridge 2-Day Challenge
Date
February 20–21, 2027

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About These Sports

This race spans more than one sport — here’s a guide to each, so you can understand what’s involved and decide if it’s the right fit. For course distances, logistics, and race-day specifics, always defer to the race organizer’s event page.

Running

From 5K to marathon, running races are an accessible entry point into endurance sport. There's a distance for every fitness level and a community at every start line.

Ultramarathon

An ultramarathon is anything beyond the standard marathon — 50K, 50-mile, 100K, 100-mile, and timed events. Crossing the line is less about speed and more about not quitting.

Frequently Asked Questions

What is the 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 is a running and ultra race held in Winter Park, Florida on February 20, 2027. It is one of the many endurance events listed on Endurance Grid, a multi-sport endurance event calendar covering running races, triathlons, HYROX, and more endurance sports across the United States. Find more running races near you or explore our sports guides to learn what race day actually feels like.
When and where is the Winter Park 50K, Marathon, Half, 10K & 5K – MileBuilt Cady Way Bridge 2-Day Challenge?
Saturday, February 20, 2027 in Winter Park, Florida at 2535 Cady Way. Check the event page for exact start times and wave schedules.
How do I register for the Winter Park 50K, Marathon, Half, 10K & 5K – MileBuilt Cady Way Bridge 2-Day Challenge?
Registration is handled through the event's registration page. Confirm pricing and distances there, and sign up.

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

Feb 20, 2027

Register