Holiday Five (Five Days, Five Distances to choose from)
Winter Park, Florida, United States · Dec 27 to Dec 31, 2026
Running races in Winter Park, Florida
2026 and 2027 race calendar. 7 upcoming, updated daily.
Map of races in Winter Park, Florida
RunningTrailCyclingTriathlonObstacleGroup of races
December 2026
February 2027
Winter Park 50K, Marathon, Half, 10K & 5K - MileBuilt Cady Way Bridge 2-Day Challenge
Winter Park, Florida, United States · Feb 20 to Feb 21, 2027
April 2027
Mission 5K
Winter Park, Florida, United States
May 2027
Sunshine Double (Two Days, Five Distances to choose from)
Winter Park, Florida, United States · May 1 to May 2, 2027
Winter Park 50K, Marathon, Half, 10K & 5K - MileBuilt Cady Way Bridge Memorial Day 3-Day Challenge
Winter Park, Florida, United States · May 29 to May 31, 2027
June 2027
Independence Double (Two Days, Five Distances to choose from)
Winter Park, Florida, United States · Jun 26 to Jun 27, 2027
September 2027
Labor Day Triple (Three Days, Five Distances to choose from)
Winter Park, Florida, United States · Sep 4 to Sep 6, 2027