Upcoming Races Near Winter Haven, FL - Matching: Trail Races

Name: AdventHealth Cool Sommer Mornings Triathlon\Duathlon\5K Series #4
Start: 2026-09-13
End: 2026-09-13
Location: Clermont

Little Big Water River 5K Trail Run/Walk

Dade City, FL

Saturday, December 6th, 2025

Featured

1 Mile

Trail

View details for race Little Big Water River 5K Trail Run/Walk

Want to feature your race?

Get your race seen first by thousands of runners

Learn More

Learn how to feature your race

CORE's 2025 Reindeer Run & Roll 5k

Altamonte Springs, FL

Saturday, December 6th, 2025

Trail

View details for race CORE's 2025 Reindeer Run & Roll 5k

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

Howey-in-the-Hills, FL

Saturday, December 13th, 2025

Trail

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

Santa's Run Fest

Winter Haven, FL

Saturday, December 20th, 2025

15K

10K

Trail

View details for race Santa's Run Fest

Holiday Five

Winter Park, FL

Saturday, December 27th, 2025

Marathon

Half

10K

Trail

View details for race Holiday Five

LRC 5k Training Program | Lakeland, FL

Lakeland, FL

Saturday, January 17th, 2026

Trail

View details for race LRC 5k Training Program | Lakeland, FL

Elevate 5k Corporate Challenge

Clermont, FL

Saturday, January 24th, 2026

Trail

View details for race Elevate 5k Corporate Challenge

Highlands County Cattlewomen's Run the Ranch

Sebring, FL

Saturday, January 31st, 2026

Trail

View details for race Highlands County Cattlewomen's Run the Ranch

AdventHealth Nighthawk Trail Run - Night Owl 5K...

Lakeland, FL

Saturday, February 7th, 2026

15K

10K

Trail

View details for race AdventHealth Nighthawk Trail Run - Night Owl 5K and Coyote 10K

The Hunt for Sasquatch

Mulberry, FL

Saturday, February 7th, 2026

10K

1 Mile

Trail

View details for race The Hunt for Sasquatch

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

Thrive & Strive 5K

Land O Lakes, FL

Saturday, February 28th, 2026

Trail

View details for race Thrive & Strive 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

LSSC Shamrock Shuffle

Clermont, FL

Saturday, March 7th, 2026

1 Mile

10K

Trail

View details for race LSSC Shamrock Shuffle

Lake Kissimmee Adventure Race & 50K

Lake Wales, FL

Saturday, March 21st, 2026

10 Miles

Ultra

Trail

View details for race Lake Kissimmee Adventure Race & 50K

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

The Florida Run @ Colt Creek State Park

Lakeland, FL

Saturday, April 11th, 2026

Half

10K

Trail

View details for race The Florida Run @ Colt Creek State Park

Sunshine Double

Winter Park, FL

Saturday, May 2nd, 2026

Marathon

Half

10K

Trail

View details for race Sunshine Double

Stomp Out Suicide Trail Race

Dade City, FL

Saturday, May 9th, 2026

10K

1 Mile

Trail

View details for race Stomp Out Suicide Trail Race

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

Explore more in Winter Haven, FL

Distances:

5K 10K Half Marathon Marathon

Months:

November December January

Tags:

Trail Boston Qualifiers Fast Courses

State:

All Florida races

Don't see your race? Add it!

Add Your Race (Free)