Florida · 5K · 10K · Half Marathon
Holiday Five Marathon
Holiday Five Marathon is a 5K, 10K, half marathon, marathon and 50K event held in Winter Park, Florida. Its next confirmed date is Sunday, December 27, 2026. About 300 runners take part across all distances.
- Race day
- December 27, 2026
- Location
- Winter Park, FL
- Field size
- ~300 runners
Race details
- Date
- Sunday, December 27, 2026
- Location
- Winter Park, Florida
- Distances
- 5K, 10K, Half Marathon, Marathon, 50K
- Field size
- About 300 runners
- Course
- Rolling
- Registration
- runsignup.com
- Official website
- wingmanrunning.com
Registration, course & weather
- Registration status
- Open
- Start time
- 6:00 AM EST
- Course profile
- Loop course; Road surface
About the Holiday Five Marathon
Five-day holiday race series in Winter Park with daily 5K, 10K, half marathon, marathon, and 50K options.
Rankings and notes
- Rankings and awards
- Adds a late-December Florida marathon/half marathon option.
- Notes
- Runner's World 2026 calendar listing; multi-day holiday race series.
More marathons in Florida
Coming up next, by confirmed date.
-
AdventHealth Presents the Central Florida Legends Marathon, Half Marathon and 5KDeBary, FLMarathonHalf Marathon5K ~6,375 runners
-
Gobbler 5K, 10K, 13.1, & 26.2 at Royal Palm Beach, FL (46)Royal Palm Beach, FLMarathonHalf Marathon5K10K
More races in Winter Park
More upcoming races in Florida
Keep exploring
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Guides from the RaceRove blog
- 8 min read How to Choose Your First Marathon A practical checklist for choosing a first marathon based on course, weather, cutoff, travel, field size and support.
- 7 min read How to Find a 5K, 10K, Half Marathon or Marathon Near You A practical way to find running races near you: pick a distance, decide how far you'll travel, read the listing properly and confirm the details before you register.
- 9 min read How to Run a Race in All 50 States How to plan a 50-state running challenge: set your own rules, group states into trips, build a calendar around the seasons, budget for it and keep track of every finish.
- Blog All guides Planning advice for finding, choosing and travelling to races.
Holiday Five Marathon: common questions
- When is the Holiday Five Marathon?
- The next confirmed date is Sunday, December 27, 2026.
- Where is the Holiday Five Marathon held?
- In Winter Park, Florida.
- What distances does the Holiday Five Marathon offer?
- 5K, 10K, Half Marathon, Marathon and 50K.
- How many people run the Holiday Five Marathon?
- About 300 runners across all of its distances. That figure is an estimate of the field size, not an entry cap.
- How do I register for the Holiday Five Marathon?
- Registration is handled by the organiser at runsignup.com. Entry fees, caps and deadlines are set there.
- Is registration open for the Holiday Five Marathon?
- Yes — registration is open. Listed fee for the longest distance, $65 (from runsignup.com, checked September 25, 2026).
- What time does the Holiday Five Marathon start?
- 6:00 AM EST.
- What is the course like at the Holiday Five Marathon?
- Loop course; Road surface.
Plan this race in RaceRove
Save it to your plan, compare it with other races, check typical race-day weather and track your 50-state progress in the interactive app.