Running races in Winter Park, FL
19 upcoming running races in Winter Park, FL — 10Ks, half marathons and marathons, with dates and field depth before you enter.
December 2026
- Sun, Dec 27Holiday Five (Five Days, Five Distances to choose from)Winter Park5K10KHalf marathonMarathon
- Mon, Dec 28Holiday Five (Five Days, Five Distances to choose from)Winter Park5K10KHalf marathonMarathon
- Tue, Dec 29Holiday Five (Five Days, Five Distances to choose from)Winter Park5K10KHalf marathonMarathon
- Wed, Dec 30Holiday Five (Five Days, Five Distances to choose from)Winter Park5K10KHalf marathonMarathon
- Thu, Dec 31Holiday Five (Five Days, Five Distances to choose from)Winter Park5K10KHalf marathonMarathon
January 2027
February 2027
April 2027
May 2027
- Sat, May 1Sunshine Double (Two Days, Five Distances to choose from)Winter Park5K10KHalf marathonMarathon
- Sun, May 2Sunshine Double (Two Days, Five Distances to choose from)Winter Park5K10KHalf marathonMarathon
- Sat, May 29Winter Park 50K, Marathon, Half, 10K & 5K – MileBuilt Cady Way Bridge Memorial Day 3-Day ChallengeWinter Park5K10KHalf marathonMarathon
- Sun, May 30Winter Park 50K, Marathon, Half, 10K & 5K – MileBuilt Cady Way Bridge Memorial Day 3-Day ChallengeWinter Park5K10KHalf marathonMarathon
- Mon, May 31Winter Park 50K, Marathon, Half, 10K & 5K – MileBuilt Cady Way Bridge Memorial Day 3-Day ChallengeWinter Park5K10KHalf marathonMarathon
June 2027
September 2027
- Sat, Sep 4Labor Day Triple (Three Days, Five Distances to choose from)Winter Park5K10KHalf marathonMarathon
- Sun, Sep 5Labor Day Triple (Three Days, Five Distances to choose from)Winter Park5K10KHalf marathonMarathon
- Mon, Sep 6Labor Day Triple (Three Days, Five Distances to choose from)Winter Park5K10KHalf marathonMarathon