Holiday Five (Five Days, Five Distances to choose from)
Winter Park, Florida, United States · Dec 27 to Dec 31, 2026
Marathons in Winter Park, Florida
2026 and 2027 race calendar. 6 upcoming, updated daily.
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
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