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Entries openVerified
Verified Sun, 11 Oct 2026
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USARunningRoad10K · 10 km / 6.2 mi50K · 50 km / 31.1 mi5K · 5 km / 3.1 miHalf · 21.1 km / 13.1 mi
Holiday Five
Winter Park, Florida, Cady Way Trailhead, 2529 Cady Way · USA
Next race day
Sun, 27 Dec 2026
5 distances · see start times below
About Holiday Five
Holiday Five is a running event in Winter Park, Florida, Cady Way Trailhead, 2529 Cady Way, United States. Recorded disciplines include 10K, 50K, 5K, half marathon. The listed surface is road. The listed organiser is Wingman Running Company. The next listed date is 27 December 2026. Check the organiser's information for entry and race-day arrangements.
Dates, starts & entry
Times are local to the race. Select the entry route for your distance.
- Official entry
Half · 21.1 km / 13.1 mi
Sun, 27 Dec 2026
Starts 06:00 EST
Entries open
Day 1 of five separately timed race days. Single-day and all-five-day booking options are available. Hand timed on a shared paved trail; tell the timer when you finish. Bring your own hydration container. Bring a light for the first half hour.
Edition source - Official entry
Marathon · 42.2 km / 26.2 mi
Sun, 27 Dec 2026
Starts 06:00 EST
Entries open
Day 1 of five separately timed race days. Single-day and all-five-day booking options are available. Hand timed on a shared paved trail; tell the timer when you finish. Bring your own hydration container. Bring a light for the first half hour.
Edition source - Official entry
10K · 10 km / 6.2 mi
Sun, 27 Dec 2026
Starts 07:00 EST
Entries open
Day 1 of five separately timed race days. Single-day and all-five-day booking options are available. Hand timed on a shared paved trail; tell the timer when you finish. Bring your own hydration container.
Edition source - Official entry
5K · 5 km / 3.1 mi
Sun, 27 Dec 2026
Starts 07:00 EST
Entries open
Day 1 of five separately timed race days. Single-day and all-five-day booking options are available. Hand timed on a shared paved trail; tell the timer when you finish. Bring your own hydration container.
Edition source - Official entry
50K · 50 km / 31.1 mi
Sun, 27 Dec 2026
Starts 06:00 EST
Entries open
Day 1 of five separately timed race days. Single-day and all-five-day booking options are available. Hand timed on a shared paved trail; tell the timer when you finish. Bring your own hydration container. Bring a light for the first half hour.
Edition source - Official entry
Half · 21.1 km / 13.1 mi
Mon, 28 Dec 2026
Starts 06:00 EST
Entries open
Day 2 of five separately timed race days. Single-day and all-five-day booking options are available. Hand timed on a shared paved trail; tell the timer when you finish. Bring your own hydration container. Bring a light for the first half hour.
Edition source - Official entry
Marathon · 42.2 km / 26.2 mi
Mon, 28 Dec 2026
Starts 06:00 EST
Entries open
Day 2 of five separately timed race days. Single-day and all-five-day booking options are available. Hand timed on a shared paved trail; tell the timer when you finish. Bring your own hydration container. Bring a light for the first half hour.
Edition source - Official entry
10K · 10 km / 6.2 mi
Mon, 28 Dec 2026
Starts 07:00 EST
Entries open
Day 2 of five separately timed race days. Single-day and all-five-day booking options are available. Hand timed on a shared paved trail; tell the timer when you finish. Bring your own hydration container.
Edition source - Official entry
5K · 5 km / 3.1 mi
Mon, 28 Dec 2026
Starts 07:00 EST
Entries open
Day 2 of five separately timed race days. Single-day and all-five-day booking options are available. Hand timed on a shared paved trail; tell the timer when you finish. Bring your own hydration container.
Edition source - Official entry
50K · 50 km / 31.1 mi
Mon, 28 Dec 2026
Starts 06:00 EST
Entries open
Day 2 of five separately timed race days. Single-day and all-five-day booking options are available. Hand timed on a shared paved trail; tell the timer when you finish. Bring your own hydration container. Bring a light for the first half hour.
Edition source - Official entry
Half · 21.1 km / 13.1 mi
Tue, 29 Dec 2026
Starts 06:00 EST
Entries open
Day 3 of five separately timed race days. Single-day and all-five-day booking options are available. Hand timed on a shared paved trail; tell the timer when you finish. Bring your own hydration container. Bring a light for the first half hour.
Edition source - Official entry
Marathon · 42.2 km / 26.2 mi
Tue, 29 Dec 2026
Starts 06:00 EST
Entries open
Day 3 of five separately timed race days. Single-day and all-five-day booking options are available. Hand timed on a shared paved trail; tell the timer when you finish. Bring your own hydration container. Bring a light for the first half hour.
Edition source
Location & race day
Listed venue / area
Cady Way Trailhead, 2529 Cady Way, Winter Park, FloridaUSA
Confirm the exact start line, parking and arrival instructions with the organiser. A listed town or postcode may cover a wider area.
About the race
Five consecutive days of low-key races on the paved Cady Way Trail, with five distances each day.
- Surface:
- Road
- Organiser:
- Wingman Running Company
Ways to enter
Compare the listed booking routes. Verified links show when they were checked.
Sun, 27 Dec 2026
Third-party prices, booking fees, allocations and refund terms can differ. Confirm the final details with the provider before paying.
Results
Public-figure or athlete-approved ATHRECS results, plus verified organiser links.
No verified results links have been added yet.
Past races
None listed yet.
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