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

Name: Labor Day Triple
Start: 2026-09-05
End: 2026-09-05
Location: Winter Park

Mayor's 5K Run/Walk

Haines City, FL

Saturday, October 4th, 2025

Featured

Trail

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

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PawPals 4 Life 5k

Sorrento, FL

Saturday, October 4th, 2025

Trail

View details for race PawPals 4 Life 5k

Lutheran Counseling Services: We Care 5K

Longwood, FL

Saturday, October 11th, 2025

Trail

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

2025 Town of Windermere Centennial Celebration ...

Windermere, FL

Saturday, October 11th, 2025

10K

Trail

View details for race 2025 Town of Windermere Centennial Celebration Orlando Health 5K/10K Run Among the Lakes

2025 Enchanted Forest Sanctuary 5K/2K Trail Run

Titusville, FL

Sunday, October 12th, 2025

Trail

View details for race 2025 Enchanted Forest Sanctuary 5K/2K Trail Run

Central 28 Monster Mash-N-Dash 5K Run and Walk

Debary, FL

Saturday, October 25th, 2025

Trail

View details for race Central 28 Monster Mash-N-Dash 5K Run and Walk

EverBe Spooktacular Sprint 5K

Orlando, FL

Sunday, October 26th, 2025

Trail

View details for race EverBe Spooktacular Sprint 5K

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

Clermont, FL

Sunday, October 26th, 2025

15K

Trail

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

DeLeon Dash 5K

De Leon Springs, FL

Saturday, November 8th, 2025

Trail

View details for race DeLeon Dash 5K

Save the Manatee 5K

Orange City, FL

Saturday, November 15th, 2025

Trail

View details for race Save the Manatee 5K

Volusia County Schools Trails to Success 5k

DeBary, FL

Sunday, November 16th, 2025

Trail

View details for race Volusia County Schools Trails to Success 5k

5K with the 5-0

Oakland, FL

Saturday, November 22nd, 2025

Trail

View details for race 5K with the 5-0

Ultra Ultras Turkey Trot 5k

Lake Wales, FL

Thursday, November 27th, 2025

Trail

View details for race Ultra Ultras Turkey Trot 5k

Trail Running Festival

New Smyrna Beach, FL

Saturday, December 13th, 2025

Ultra

Trail

View details for race Trail Running Festival

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

Wild Florida 5K

Orlando, FL

Saturday, January 31st, 2026

Trail

View details for race Wild Florida 5K

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

Inua 5k Run and Walk

Orlando, FL

Saturday, February 28th, 2026

Trail

View details for race Inua 5k Run and Walk

Inua 5k Run and Walk

Winter Park, 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

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

Sunshine Double

Winter Park, FL

Saturday, May 2nd, 2026

Marathon

Half

10K

Trail

View details for race Sunshine Double

The Florida Run LEFTOVER Trail Race

Clermont, FL

Saturday, June 13th, 2026

Trail

View details for race The Florida Run LEFTOVER Trail Race

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

Labor Day Triple

Winter Park, FL

Saturday, September 5th, 2026

Marathon

Half

10K

Trail

View details for race Labor Day Triple

Explore more in Winter Park, FL

Distances:

5K 10K Half Marathon Marathon

Months:

October November December

Tags:

Trail Boston Qualifiers Fast Courses

State:

All Florida races

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