Holiday Five (Five Days, Five Distances to choose from)
Winter Park, Central Florida
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26.2 miles
Next up: Holiday Five (Five Days, Five Distances to choose from) on December 27, 2026. Every race below links to registration.
6
Upcoming Marathons
10
All Winter Park races
Winter Park, Central Florida
Winter Park, Central Florida
Winter Park, Central Florida
Winter Park, Central Florida
Winter Park, Central Florida
Winter Park, Central Florida
Winter Park has 6 upcoming Marathon races on the calendar, running from December 27, 2026 through September 4, 2027. New events are added as organizers open registration.
The next Marathon in Winter Park is Holiday Five (Five Days, Five Distances to choose from) on December 27, 2026. Click the race for course details and the registration link.
Open any race above and click Register. You will go straight to the official registration page, usually on RunSignUp. Entry fees rise as race day approaches, so early registration is cheaper.
October through March is prime racing season in Winter Park, with cooler mornings and lower humidity. Summer races start early, often before 7am, to beat the heat.
Winter Park runners have 6 Marathon races to pick from this season, part of 10 upcoming races across all distances in the city. Florida courses are flat and fast, so a Marathon here is a good place to chase a personal best.
Register early. Most Winter Park races raise their entry fee two or three times before race day, and popular events sell out. Every card above goes straight to the official registration page.
Browse everything running in Winter Park, compare Florida marathon races, or submit your race to get listed for free.