Running Races in Winter Park, Florida — 2026

There are 7 running races in Winter Park, Florida in 2026. The next is the Holiday Five on December 27. Distances include marathons, ultras, 5K races.

Holiday Five

Sun, Dec 27 · Winter Park, FL Winter Park
Road Holiday Five 5K, Day 2Holiday Five 5K, Day 5Holiday Five 5K, Day 3 +27
From $30 Open
Register →

Mission 5K

Sat, Apr 24 · Winter Park, FL Winter Park
Road 5K Run or Walk1 mile Run or Walk
From $35 Open
Register →

Sunshine Double

Sat, May 1 · Winter Park, FL Winter Park
Road Sunshine Double 5K, Day 1Sunshine Double 5K, Day 2Sunshine Double 5K, both days +27
From $30 Open
Register →

Labor Day Triple

Sat, Sep 4 · Winter Park, FL Winter Park
Road Labor Day Triple, 5K, Day 3Labor Day Triple, 5K, Day 1Labor Day Triple, 5K, Day 2 +37
From $30 Open 50 spots left
Register →

All Florida Races

View all running races in Florida →