Upcoming Races Near Kissimmee, FL - Matching: Trail Races

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

LSSC Shamrock Shuffle

Clermont, FL

Saturday, March 7th, 2026

Featured

1 Mile

10K

Trail

View details for race LSSC Shamrock Shuffle

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The Spring Rising

Oviedo, FL

Saturday, March 21st, 2026

1 Mile

10K

Trail

View details for race The Spring Rising

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

Sunflower 5K Run and Walk

Longwood, FL

Sunday, March 29th, 2026

Trail

View details for race Sunflower 5K Run and Walk

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

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

Turkey Creek 5K Trail Run

Palm Bay, FL

Saturday, May 23rd, 2026

Trail

View details for race Turkey Creek 5K Trail 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

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

Save the Manatee 5K

Orange City, FL

Sunday, November 15th, 2026

Trail

View details for race Save the Manatee 5K

5K with the 5-0

Oakland, FL

Saturday, November 21st, 2026

Trail

View details for race 5K with the 5-0

Ultra Ultras Turkey Trot 5k

Lake Wales, FL

Thursday, November 26th, 2026

Trail

View details for race Ultra Ultras Turkey Trot 5k

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 Kissimmee, FL

Distances:

5K 10K Half Marathon Marathon

Months:

March April May

Tags:

Trail Boston Qualifiers Fast Courses

State:

All Florida races

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