Holiday Five
calendar_today December 27, 2026
location_on Winter Park, Central Florida
31 MilesMarathonHalf Marathon10K +1 more
13.1 miles
Half Marathon Races in Winter Park, FL
Next up: Holiday Five on December 27, 2026. Every race below links to registration.
6
Upcoming Half Marathons
8
All Winter Park races
Upcoming Half Marathon Races in Winter Park
MileBuilt 2-Day Bridge Challenge
calendar_today February 20, 2027
location_on Winter Park, Central Florida
50KMarathonHalf Marathon10K +1 more
Sunshine Double
calendar_today May 1, 2027
location_on Winter Park, Central Florida
Half Marathon10K5K31 Miles +1 more
MileBuilt 3-Day Memorial Day Bridge Challenge
calendar_today May 29, 2027
location_on Winter Park, Central Florida
50KMarathonHalf Marathon10K +1 more
Independence Double
calendar_today June 26, 2027
location_on Winter Park, Central Florida
Half Marathon5K10KMarathon +1 more
Labor Day Triple
calendar_today September 4, 2027
location_on Winter Park, Central Florida
Half Marathon10K5KMarathon +1 more
Other Race Distances in Winter Park
Half Marathon Races Near Winter Park
Winter Park Half Marathon FAQs
How many Half Marathon races are in Winter Park, FL? expand_more
Winter Park has 6 upcoming Half Marathon races on the calendar, running from December 27, 2026 through September 4, 2027. New events are added as organizers open registration.
What is the next Half Marathon in Winter Park? expand_more
The next Half Marathon in Winter Park is Holiday Five on December 27, 2026. Click the race for course details and the registration link.
How do I register for a Half Marathon in Winter Park? expand_more
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.
When is the best time of year to run a Half Marathon in Winter Park? expand_more
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.
Running a Half Marathon in Winter Park
Winter Park runners have 6 Half Marathon races to pick from this season, part of 8 upcoming races across all distances in the city. Florida courses are flat and fast, so a Half 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 half marathons statewide,find a half marathon near Winter Park in the next towns over, or submit your race to get listed for free.