29 Upcoming Races Near Winter Springs, FL - Matching: Trail Races

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

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

Summer Sizzler- Orlando

Minneola, FL

Sunday, August 2nd, 2026

1 Mile

10K

Trail

View details for race Summer Sizzler- Orlando

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

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

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

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

Running Wild 5K

Melbourne, FL

Sunday, September 27th, 2026

Trail

View details for race Running Wild 5K

Mayor's 5K Run/Walk

Haines City, FL

Saturday, October 3rd, 2026

Trail

View details for race Mayor's 5K Run/Walk

Lutheran Counseling Services: We Care 5K

Longwood, FL

Saturday, October 10th, 2026

Trail

View details for race Lutheran Counseling Services: We Care 5K

2026 Orlando Health Town of Windermere Run Amon...

Windermere, FL

Saturday, October 10th, 2026

10K

Trail

View details for race 2026 Orlando Health Town of Windermere Run Among the Lakes 5K & 10K

DeLeon Dash 5K

De Leon Springs, FL

Saturday, October 17th, 2026

Trail

View details for race DeLeon Dash 5K

PawPals Endeavor: Spoooky Edition 2026 and PawP...

Sorrento, FL

Saturday, October 24th, 2026

1 Mile

Trail

View details for race PawPals Endeavor: Spoooky Edition 2026 and 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

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

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

Ancient Oaks 100-Mile Endurance Run

Titusville, FL

Saturday, December 19th, 2026

Ultra

Trail

Fast

View details for race Ancient Oaks 100-Mile Endurance Run

Holiday Five

Winter Park, FL

Sunday, December 27th, 2026

Ultra

Marathon

Half

Trail

View details for race Holiday Five

Wild Florida 5K

Orlando, FL

Saturday, January 30th, 2027

Trail

View details for race Wild Florida 5K

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

Apopka, FL

Saturday, February 13th, 2027

Ultra

Half

Trail

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

Tracked Chair Adventures -- Run for the Woods

Sorrento, FL

Sunday, February 14th, 2027

Trail

View details for race Tracked Chair Adventures -- Run for the Woods

Tomoka Brave, Strong & Healthy 5K Run/Walk

Ormond Beach, FL

Saturday, February 27th, 2027

Trail

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

Inua 5k

Orlando, FL

Saturday, February 27th, 2027

Trail

View details for race Inua 5k

LSSC Shamrock Shuffle

Clermont, FL

Saturday, March 13th, 2027

1 Mile

10K

Trail

View details for race LSSC Shamrock Shuffle

The Spring Rising

Oviedo, FL

Saturday, March 20th, 2027

1 Mile

10K

Trail

View details for race The Spring Rising

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

Clermont, FL

Sunday, March 21st, 2027

Half

10K

Trail

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

Sunshine Double

Winter Park, FL

Saturday, May 1st, 2027

Ultra

Marathon

Half

Trail

View details for race Sunshine Double

Independence Double

Winter Park, FL

Saturday, June 26th, 2027

10K

Half

Trail

View details for race Independence Double

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Oviedo Lake Mary Winter Park Orlando DeBary Deltona All Florida races