Upcoming Races Near Longwood, FL - Matching: Trail Races

Name: Holiday Five
Start: 2026-12-27
End: 2026-12-27
Location: Winter Park

Grace Race 5K & 1 Mile Run/Walk

Boca Raton, FL

Saturday, February 14th, 2026

Featured

1 Mile

View details for race Grace Race 5K & 1 Mile Run/Walk

Want to feature your race?

Get your race seen first by thousands of runners

Learn More

Learn how to feature your race

AdventHealth Lake Apopka Scenic Trail 30K Run, ...

Apopka, FL

Sunday, February 15th, 2026

Ultra

Trail

View details for race AdventHealth Lake Apopka Scenic Trail 30K Run, 8 Miler & 5K

Honoring the Fallen 5K

Clermont, FL

Saturday, February 21st, 2026

Trail

View details for race Honoring the Fallen 5K

Running with the Herd 5k

The Villages, FL

Saturday, February 21st, 2026

Trail

View details for race Running with the Herd 5k

Inua 5k Run and Walk

Winter Park, FL

Saturday, February 28th, 2026

Trail

View details for race Inua 5k Run and Walk

Inua 5k Run and Walk

Orlando, FL

Saturday, February 28th, 2026

Trail

View details for race Inua 5k Run and Walk

Tomoka Brave, Strong & Healthy 5K Run/Walk

Ormond Beach, FL

Saturday, March 7th, 2026

Trail

View details for race Tomoka Brave, Strong & Healthy 5K Run/Walk

GR-8 Hour & 5k Trail Race

Ormond Beach, FL

Saturday, March 14th, 2026

Code:Happy Trails

Trail

View details for race GR-8 Hour & 5k Trail Race

The Spring Rising

Oviedo, FL

Saturday, March 21st, 2026

1 Mile

10K

Trail

View details for race The Spring Rising

AdventHealth Lake Minneola Half Marathon, 10K a...

Clermont, FL

Sunday, March 22nd, 2026

Half

10K

Trail

View details for race AdventHealth Lake Minneola Half Marathon, 10K and 5K

Sunflower 5K Run and Walk

Longwood, FL

Sunday, March 29th, 2026

Trail

View details for race Sunflower 5K Run and Walk

Pat & Ed Northey 5K and 10K River Run

DeBary, FL

Saturday, April 11th, 2026

10K

Trail

View details for race Pat & Ed Northey 5K and 10K River Run

The Florida Run LEFTOVER Trail Race

Clermont, FL

Saturday, June 13th, 2026

Trail

View details for race The Florida Run LEFTOVER Trail Race

AdventHealth Cool Sommer Mornings Triathlon-Dua...

Clermont, FL

Sunday, June 14th, 2026

Ultra

Trail

View details for race AdventHealth Cool Sommer Mornings Triathlon-Duathlon-5K Series #1

AdventHealth Clermont Freedom 5K presented by L...

Clermont, FL

Saturday, July 4th, 2026

Trail

View details for race AdventHealth Clermont Freedom 5K presented by Live Trends Design Group

$AdventHealth Cool Sommer Mornings Triathlon\Duathlon\5K Series #2 logo$

AdventHealth Cool Sommer Mornings Triathlon\Dua...

Clermont, FL

Sunday, July 12th, 2026

Ultra

Trail

View details for race AdventHealth Cool Sommer Mornings Triathlon\Duathlon\5K Series #2

$AdventHealth Cool Sommer Mornings Triathlon\Duathlon\5K Series #3 logo$

AdventHealth Cool Sommer Mornings Triathlon\Dua...

Clermont, FL

Sunday, August 9th, 2026

Ultra

Trail

View details for race AdventHealth Cool Sommer Mornings Triathlon\Duathlon\5K Series #3

Labor Day Triple

Winter Park, FL

Saturday, September 5th, 2026

Marathon

Half

10K

Trail

View details for race Labor Day Triple

$AdventHealth Cool Sommer Mornings Triathlon\Duathlon\5K Series #4 logo$

AdventHealth Cool Sommer Mornings Triathlon\Dua...

Clermont, FL

Sunday, September 13th, 2026

Ultra

Trail

View details for race AdventHealth Cool Sommer Mornings Triathlon\Duathlon\5K Series #4

PawPals 4 Life 5k

Sorrento, FL

Saturday, October 24th, 2026

Trail

View details for race PawPals 4 Life 5k

AdventHealth Clermont Clay 15K & 5K presented b...

Clermont, FL

Sunday, October 25th, 2026

15K

Trail

View details for race AdventHealth Clermont Clay 15K & 5K presented by LiveTrends Design Group

The Rising

Oviedo, FL

Saturday, October 31st, 2026

1 Mile

10K

Trail

View details for race The Rising

The Florida Run @ Lake Louisa State Park

Clermont, FL

Saturday, November 7th, 2026

Half

10K

Trail

View details for race The Florida Run @ Lake Louisa State Park

AdventHealth Howey-in-the-Hills Reindeer Dash 5...

Howey-in-the-Hills, FL

Saturday, December 12th, 2026

Trail

View details for race AdventHealth Howey-in-the-Hills Reindeer Dash 5K presented by LiveTrends Design Group

Holiday Five

Winter Park, FL

Sunday, December 27th, 2026

Ultra

Marathon

Half

Trail

View details for race Holiday Five

Explore more in Longwood, FL

Distances:

5K 10K Half Marathon Marathon

Months:

February March April

Tags:

Trail Boston Qualifiers Fast Courses

State:

All Florida races

Don't see your race? Add it!

Add Your Race (Free)