Holiday Five (Five Days, Five Distances to choose from)
calendar_today December 27, 2026
location_on Winter Park, Central Florida
Half Marathon5K31 MilesMarathon +1 more
Central Florida
Upcoming Races in Winter Park, FL
Next up: Holiday Five (Five Days, Five Distances to choose from) on December 27, 2026. Every race below links to registration.
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Upcoming Races
Upcoming Races in Winter Park by Month
calendar_month December 2026
calendar_month January 2027
calendar_month February 2027
Winter Park 50K, Marathon, Half, 10K & 5K – MileBuilt Cady Way Bridge 2-Day Challenge
calendar_today February 20, 2027
location_on Winter Park, Central Florida
50KMarathonHalf Marathon10K +1 more
calendar_month March 2027
directions_run
calendar_month April 2027
calendar_month May 2027
Sunshine Double (Two Days, Five Distances to choose from)
calendar_today May 1, 2027
location_on Winter Park, Central Florida
Marathon31 MilesHalf Marathon10K +1 more
directions_run
Winter Park 50K, Marathon, Half, 10K & 5K – MileBuilt Cady Way Bridge Memorial Day 3-Day Challenge
calendar_today May 29, 2027
location_on Winter Park, Central Florida
50K10K5KMarathon +1 more
calendar_month June 2027
Independence Double (Two Days, Five Distances to choose from)
calendar_today June 26, 2027
location_on Winter Park, Central Florida
10KHalf Marathon31.06 MilesMarathon +1 more
calendar_month September 2027
Labor Day Triple (Three Days, Five Distances to choose from)
calendar_today September 4, 2027
location_on Winter Park, Central Florida
Half Marathon10K5KMarathon +1 more
Winter Park Race FAQs
What races are coming up in Winter Park, FL? expand_more
Winter Park has 10 upcoming races: 5K (9), 10K (7), Half Marathon (6), Marathon (6), Ultra (6), 1 Mile (1). The next one is Holiday Five (Five Days, Five Distances to choose from) on December 27, 2026. Every listing above links to registration.
Are there 5K races in Winter Park? expand_more
Yes. Winter Park has 9 upcoming 5Ks. See the full list: Winter Park 5K races.
How do I register for a race in Winter Park? expand_more
Open any race and click Register to reach the official registration page, usually on RunSignUp. Fees go up as race day gets closer, so signing up early saves money.
When is race season in Winter Park? expand_more
Most Winter Park races fall between October and March, when mornings are cool and dry. Summer events start early to beat the heat, and many switch to evening or virtual formats.
Racing in Winter Park, Florida
This is every Winter Park race with registration open, updated daily: 5K (9), 10K (7), Half Marathon (6), Marathon (6), Ultra (6), 1 Mile (1). Courses here are flat, so Winter Park is a good place to chase a personal best at any distance.
Register early. Most 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.
See everything running in Winter Park, see all Florida road races, browse the full Florida calendar with filters, or submit your race to get listed for free.