Holiday Five – Winter Park, FL 2026
Date
December 27, 2026
Location
Winter Park, FL
Venue
Cady Way Trail Head
Start Time
6:00 AM
Entry Fee
$30.00 – $390.00
Events
Holiday Five 50K, all five days, Holiday Five 50K, Day 1, Holiday Five 50K, Day 2, Holiday Five 50K, Day 3, Holiday Five 50K, Day 4, Holiday Five 50K, Day 5
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PLACE : 2529 Cady Way, Winter Park, FL 32792 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 marathon—6:00 am; 5K and 10K—7:00 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 low—very low—so that your disappointment will be minimal. But wait! We have easy logistics, great course, and an abundance of friendliness. Also, very convenient parking—pass your car every lap. If you’re still interested, here’s 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 ch
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