Running Races in Winter Park, Florida 2026 | Browse All Races

There are 5 running races in Winter Park, Florida in 2026. The next is the Labor Day Triple on September 5. Distances include marathons, ultras.

Sat, Sep 5 · Winter Park, FL Winter Park

Road Labor Day Triple, 5K, Day 2Labor Day Triple, 5K, Day 3Labor Day Triple, 5K, Day 1 +17

From $30 Open Closing Soon 50 spots left

Sun, Dec 27 · Winter Park, FL Winter Park

Road Holiday Five 5K, Day 5Holiday Five 5K, Day 4Holiday Five 5K, all five days +27

From $30 Open

Sat, Feb 20 · Winter Park, FL Winter Park

Ultra 5K - Day 2 (Sunday)5K - Day 1 (Saturday)10K - Day 2 (Sunday) +7

From $35 Open

Sat, May 1 · Winter Park, FL Winter Park

Road Sunshine Double 5K, both daysSunshine Double 5K, Day 1Sunshine Double 5K, Day 2 +27

From $30 Open

Sat, Jun 26 · Winter Park, FL Winter Park

Road 5K, Sunday5K, Saturday5K, Saturday +27

From $30 Open

Running Races in Winter Park, Florida — 2026