Winter Park, FL
Holiday Five (Five Days, Five Distances to choose from)
- Date
- First start6:00 AM EST
- LocationCady Way Trail Head, Winter Park, FL 32792
- DistancesUltra · Marathon · Half Marathon · 10K · 5K
- SurfaceTrail
Bib Scout Report
- Trail
- Boston Qualifier
| Event | Distance | Start | Current fee | Next increase |
|---|---|---|---|---|
| Holiday Five 50K, all five days | Ultra | 6:00 AM EST | $350 | $390 on |
| Holiday Five 50K, Day 1 | Ultra | 6:00 AM EST | $75 | $85 on |
| Holiday Five 50K, Day 2 | Ultra | 6:00 AM EST | $75 | $85 on |
| Holiday Five 50K, Day 3 | Ultra | 6:00 AM EST | $75 | $85 on |
| Holiday Five 50K, Day 4 | Ultra | 6:00 AM EST | $75 | $85 on |
| Holiday Five 50K, Day 5 | Ultra | 6:00 AM EST | $75 | $85 on |
| Holiday Five Marathon, all five days | Marathon | 6:00 AM EST | $300 | $340 on |
| Holiday Five Marathon, Day 1 | Marathon | 6:00 AM EST | $65 | $75 on |
| Holiday Five Marathon, Day 2 | Marathon | 6:00 AM EST | $65 | $75 on |
| Holiday Five Marathon, Day 3 | Marathon | 6:00 AM EST | $65 | $75 on |
| Holiday Five Marathon, Day 4 | Marathon | 6:00 AM EST | $65 | $75 on |
| Holiday Five Marathon, Day 5 | Marathon | 6:00 AM EST | $65 | $75 on |
| Holiday Five Half Marathon, all five days | Half Marathon | 6:00 AM EST | $250 | $290 on |
| Holiday Five Half Marathon, Day 1 | Half Marathon | 6:00 AM EST | $55 | $65 on |
| Holiday Five Half Marathon, Day 2 | Half Marathon | 6:00 AM EST | $55 | $65 on |
| Holiday Five Half Marathon, Day 3 | Half Marathon | 6:00 AM EST | $55 | $65 on |
| Holiday Five Half Marathon, Day 4 | Half Marathon | 6:00 AM EST | $55 | $65 on |
| Holiday Five Half Marathon, Day 5 | Half Marathon | 6:00 AM EST | $55 | $65 on |
| Holiday Five 10K, all five days | 10K | 7:00 AM EST | $175 | $200 on |
| Holiday Five 10K, Day 1 | 10K | 7:00 AM EST | $40 | $45 on |
| Holiday Five 10K, Day 2 | 10K | 7:00 AM EST | $40 | $45 on |
| Holiday Five 10K, Day 3 | 10K | 7:00 AM EST | $40 | $45 on |
| Holiday Five 10K, Day 4 | 10K | 7:00 AM EST | $40 | $45 on |
| Holiday Five 10K, Day 5 | 10K | 7:00 AM EST | $40 | $45 on |
| Holiday Five 5K, all five days | 5K | 7:00 AM EST | $125 | $150 on |
| Holiday Five 5K, Day 1 | 5K | 7:00 AM EST | $30 | $35 on |
| Holiday Five 5K, Day 2 | 5K | 7:00 AM EST | $30 | $35 on |
| Holiday Five 5K, Day 3 | 5K | 7:00 AM EST | $30 | $35 on |
| Holiday Five 5K, Day 4 | 5K | 7:00 AM EST | $30 | $35 on |
| Holiday Five 5K, Day 5 | 5K | 7:00 AM EST | $30 | $35 on |
Scouted from the official RunSignup listing. Fees shown exclude processing fees.Merit badges are detected from the organizer’s description. Dates, courses, and prices can change — confirm on the registration page.
About Holiday Five (Five Days, Five Distances to choose from)
PLACE : 2529 Cady Way, Winter Park, FL 32792 DESCRIPTION : Holiday Five, December 27, 28, 29, 30, 31, 2026 What: 5 Distances and 5 days to choose from. 50K, Marathon, Half marathon, 10K, and 5K available each day. Where: Cady Way Trail Head, 2529 Cady Way, Winter Park, FL 32792 Start Times: 50K, Marathon, and Half marathon—6:00 am; 5K and 10K—7:00 am. Time limit: 9.5 hours Parking: Cady Way Trailhead, near the Cady Way Pool. GPS coordinates: N 28.59458, W -081.31670 WAIT! Before you register, read everything below. Here are the main points: Races are not chip timed. We are old-fashioned hand timed. Courses are not certified. No Boston qualifier. No age group awards, no t-shirts, no useless bling. Cupless—bring your own bottle These are low-key, casual, fun events. GREAT for first timers! These are not certified or sanctioned courses —meaning, NOT a Boston qualifier. Don’t expect much…
More in Winter Park: Ultra races · Marathon races · Half Marathon races · 10K races · 5K races