Holiday Five
- Date Sun 27th December 2026 - Thu 31st December 2026
- Time 6:00AM EST
- Location Winter Park, Florida
- Price $32.80 - $368.50
- Races 30 races
- Distances Ultra, Marathon, Half Marathon, 10km, 5km
Event summary
Participants can expect a friendly and supportive atmosphere on the flat, paved, and partially shaded urban run/bike trail. With generous time limits and basic support, this low-key event is perfect for those looking for a casual running experience without the pressure of age group awards or elaborate swag. Enjoy the simplicity of the courses, the camaraderie of fellow runners, and the convenience of easy parking right by the start/finish area. Don’t miss out on this fantastic opportunity to embrace the joy of running during the holiday season!
Organiser's Description
DESCRIPTION: Holiday Five, December 27, 28, 29, 30, 31, 2025
What: 5 Distances, 5 days. 50K, Marathon, Half marathon, 10K, and 5K each day.
Where: Cady Way Trail Head, 2529 Cady Way, Winter Park, FL 32792
Start Times: 50K, Marathon, and Half marathon6:00 am; 5K and 10K7:00 am.
Time limit: 9.5 hours (or so)
Parking: Cady Way Trailhead, near the Cady Way Pool. GPS coordinates:
N 28.59458, W -081.31670
WARNING: Before you continue, be warned that these are low-key, bare bones, casual events. Set your expectations lowvery lowso that your disappointment will be minimal. But wait! We have easy logistics, great course, and an abundance of friendliness. Also, very convenient parkingpass your car every lap. If youre still interested, heres what to expect.
You WILL NOT get age group awards, a cleverly designed t-shirt or hat, great bling (actually, any bling), cute reusable race bag filled with goodies, spectators lining the course, crowds cheering you in, hearty food at the finish, exciting music, or a party afterward.
You WILL get LOW ENTRY FEES, courses that are guaranteed not short, a nice finishers medal, basic support (see below), a VERY generous time limit, and lots of friendly support from staff and runners. Also, convenient locations for supporters.
START/FINISH AND AID STATION: The start and finish are in a small pavilion, where you may leave a drop bag. This is also the aid station, which you will pass twice each lap. (More about laps below.) We will provide water, Gatorade, sodas, and light sweet and salty snacks, including pickles and pickle juice.
COURSES: The paved, urban run/bike trail is flat and partly shaded. This is an open course, and includes two street crossings. You are responsible for crossing safely. The 50K/marathon/half marathon course is a double out-and-back loop of approximately 2.2 miles; marathon 12 loops, half marathon 6 loops, 50K 14 loops plus 2 "baby" loops. The 5K/10K course is approximately 1.55 miles, 2 and 4 loops respectively. Turn arounds will be clearly marked. The trail is popular with local residents, so be prepared to share. For more information about the courses, see DETAILED COURSE DESCRIPTION above.
FINISH: When you are finished, RING THE BELL at the timing table and let the timer know you're finished. That's the only way to get an accurate time. Remember we are hand-timed. If you don't tell us, we won't know.
CUPLESS: Bring your own hydration devicewater bottle, hydration belt/pack. There will be a table at the start/finish for your bottles. (We will have small cups for the soda.)
LIGHT: If you start at 6:00, you will need a light for the first half hour.
VOLUNTEERS NEEDED: Each volunteer day earns a free race entry for yourself or someone else for either one long race (50K, marathon, or half marathon) or for two short races (5K or 10K). Contact Bettie at bettiemw@gmail.com.
BMW Running Company
Races
-
Holiday Five 50K, All Five Days
Incl. $18.50 Fee
Sun 27th December 2026 (6:00AM EST)
$368.50
-
Holiday Five 50K, Day 1
Incl. $5.50 Fee
Sun 27th December 2026 (6:00AM EST)
$80.50
-
Holiday Five 50K, Day 2
Incl. $5.50 Fee
Mon 28th December 2026 (6:00AM EST)
$80.50
-
Holiday Five 50K, Day 3
Incl. $5.50 Fee
Tue 29th December 2026 (6:00AM EST)
$80.50
-
Holiday Five 50K, Day 4
Incl. $5.50 Fee
Wed 30th December 2026 (6:00AM EST)
$80.50
-
Holiday Five 50K, Day 5
Incl. $5.50 Fee
Thu 31st December 2026 (6:00AM EST)
$80.50
-
Holiday Five Marathon, All Five Days
Incl. $16.00 Fee
Sun 27th December 2026 (6:00AM EST)
$316.00
-
Holiday Five Marathon, Day 1
Incl. $4.90 Fee
Sun 27th December 2026 (6:00AM EST)
$69.90
-
Holiday Five Marathon, Day 2
Incl. $4.90 Fee
Mon 28th December 2026 (6:00AM EST)
$69.90
-
Holiday Five Marathon, Day 3
Incl. $4.90 Fee
Tue 29th December 2026 (6:00AM EST)
$69.90
-
Holiday Five Marathon, Day 4
Incl. $4.90 Fee
Wed 30th December 2026 (6:00AM EST)
$69.90
-
Holiday Five Marathon, Day 5
Incl. $4.90 Fee
Thu 31st December 2026 (6:00AM EST)
$69.90
-
Holiday Five Half Marathon, All Five Days
Incl. $13.50 Fee
Sun 27th December 2026 (6:00AM EST)
$263.50
-
Holiday Five Half Marathon, Day 1
Incl. $4.30 Fee
Sun 27th December 2026 (6:00AM EST)
$59.30
-
Holiday Five Half Marathon, Day 2
Incl. $4.30 Fee
Mon 28th December 2026 (6:00AM EST)
$59.30
-
Holiday Five Half Marathon, Day 3
Incl. $4.30 Fee
Tue 29th December 2026 (6:00AM EST)
$59.30
-
Holiday Five Half Marathon, Day 4
Incl. $4.30 Fee
Wed 30th December 2026 (6:00AM EST)
$59.30
-
Holiday Five Half Marathon, Day 5
Incl. $4.30 Fee
Thu 31st December 2026 (6:00AM EST)
$59.30
-
Holiday Five 10K, All Five Days
Incl. $11.50 Fee
Sun 27th December 2026 (7:00AM EST)
$186.50
-
Holiday Five 10K, Day 1
Incl. $3.40 Fee
Sun 27th December 2026 (7:00AM EST)
$43.40
-
Holiday Five 10K, Day 2
Incl. $3.40 Fee
Mon 28th December 2026 (7:00AM EST)
$43.40
-
Holiday Five 10K, Day 3
Incl. $3.40 Fee
Tue 29th December 2026 (7:00AM EST)
$43.40
-
Holiday Five 10K, Day 4
Incl. $3.40 Fee
Wed 30th December 2026 (7:00AM EST)
$43.40
-
Holiday Five 10K, Day 5
Incl. $3.40 Fee
Thu 31st December 2026 (7:00AM EST)
$43.40
-
Holiday Five 5K, All Five Days
Incl. $8.50 Fee
Sun 27th December 2026 (7:00AM EST)
$133.50
-
Holiday Five 5K, Day 1
Incl. $2.80 Fee
Sun 27th December 2026 (7:00AM EST)
$32.80
-
Holiday Five 5K, Day 2
Incl. $2.80 Fee
Mon 28th December 2026 (7:00AM EST)
$32.80
-
Holiday Five 5K, Day 3
Incl. $2.80 Fee
Tue 29th December 2026 (7:00AM EST)
$32.80
-
Holiday Five 5K, Day 4
Incl. $2.80 Fee
Wed 30th December 2026 (7:00AM EST)
$32.80
-
Holiday Five 5K, Day 5
Incl. $2.80 Fee
Thu 31st December 2026 (7:00AM EST)
$32.80
Reviews
Done this event?
First-hand event reviews from people who have been there, done that and got the breathable T-shirt, really help everyone choose their next event.
Add a reviewLocation
Cady Way Trail Head, 2529 Cady Way, Winter Park, 32792, FL, United States
Who's In
See who else is doing this event
Be the first
No-one has marked this event as 'Doing' or 'Maybe' yet. Will you be the first?
Holiday Five