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

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

Holiday Five (Five Days, Five Distances to choose from)

Sun, Dec 27 · Winter Park, FL Winter Park

Road Holiday Five 5K, Day 4Holiday Five 5K, all five daysHoliday Five 5K, Day 2 +27

From $30 Open

Winter Park 50K, Marathon, Half, 10K & 5K – MileBuilt Cady Way Bridge 2-Day Challenge

Sat, Feb 20 · Winter Park, FL Winter Park

Ultra Bridge 5K - Day 1Bridge 5K - Day 2Bridge 10K - Day 1 +7

From $35 Open

Mission 5K

Sat, Apr 24 · Winter Park, FL Winter Park

Road 5K Run or Walk1 mile Run or Walk

From $35 Open

Sunshine Double (Two Days, Five Distances to choose from)

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

Winter Park 50K, Marathon, Half, 10K & 5K – MileBuilt Cady Way Bridge Memorial Day 3-Day Challenge

Sat, May 29 · Winter Park, FL Winter Park

Ultra Memorial Bridge 5K - Day 2Memorial Bridge 5K - Day 3Memorial Bridge 5K - Day 1 +12

From $35 Open

Independence Double (Two Days, Five Distances to choose from)

Sat, Jun 26 · Winter Park, FL Winter Park

Road 5K, Saturday5K, both days5K, both days +27

From $30 Open

Labor Day Triple (Three Days, Five Distances to choose from)

Sat, Sep 4 · Winter Park, FL Winter Park

Road Labor Day Triple, 5K, Day 2Labor Day Triple, 5K, all three daysLabor Day Triple, 5K, Day 3 +37

From $30 Open 50 spots left

Running Races in Winter Park, Florida — 2026

Holiday Five (Five Days, Five Distances to choose from)

Winter Park 50K, Marathon, Half, 10K & 5K – MileBuilt Cady Way Bridge 2-Day Challenge

Mission 5K

Sunshine Double (Two Days, Five Distances to choose from)

Winter Park 50K, Marathon, Half, 10K & 5K – MileBuilt Cady Way Bridge Memorial Day 3-Day Challenge

Independence Double (Two Days, Five Distances to choose from)

Labor Day Triple (Three Days, Five Distances to choose from)

All Florida Races