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
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. [enrich 2026-09-24] Replaced generic Runner's World calendar link with the actual official organizer site (Wingman Running Company, wingmanrunning.com) and official RunSignUp registration URL. No genuine runner reviews found on RaceRaves, MarathonGuide, BibRave, or Reddit as of enrichment date - all aggregator listings simply…
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Guides from the RaceRove blog
- 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.
- 8 min read How to Choose the Best Half Marathon for a PR, Racecation or 50-State Challenge The best half marathon depends on what you want from it. How to choose a course for a personal record, a race worth travelling for, or an efficient stop on a 50-state challenge.
- 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.
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.