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

Most popular races in Florida →

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

Organize a race? Add it free — over 100,000 runners use Find The Run every month.

Add it free Boost it

CORE's 2026 Reindeer Run & Roll 5k

Altamonte Springs, FL

Saturday, December 5th, 2026

Trail

View details for race CORE's 2026 Reindeer Run & Roll 5k

Lights & Laces 5K

Lake Wales, FL

Saturday, December 12th, 2026

Trail

View details for race Lights & Laces 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

Santa's Run Fest

Winter Haven, FL

Saturday, December 19th, 2026

15K

10K

Trail

View details for race Santa's Run Fest

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 (Five Days, Five Distances to choo...

Winter Park, FL

Sunday, December 27th, 2026

Ultra

Marathon

Half

Trail

View details for race Holiday Five (Five Days, Five Distances to choose from)

Florida Outlaw Ultra

Ocklawaha, FL

Saturday, January 2nd, 2027

Ultra

Half

Trail

View details for race Florida Outlaw Ultra

OUTLAST ORLANDO

Clermont, FL

Saturday, January 16th, 2027

Trail

Fast

View details for race OUTLAST ORLANDO

DeBary 50K, Marathon, Half, 10K & 5K – MileBuil...

DeBary, FL

Saturday, January 23rd, 2027

Ultra

Marathon

Half

Trail

View details for race DeBary 50K, Marathon, Half, 10K & 5K – MileBuilt Gemini Springs 2-Day Challenge

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

Winter Park 50K, Marathon, Half, 10K & 5K – Mil...

Winter Park, FL

Saturday, February 20th, 2027

Ultra

Marathon

Half

Trail

View details for race Winter Park 50K, Marathon, Half, 10K & 5K – MileBuilt Cady Way Bridge 2-Day Challenge

Inua 5k

Orlando, FL

Saturday, February 27th, 2027

Trail

View details for race Inua 5k

Running with the Herd 5k

The Villages, FL

Saturday, February 27th, 2027

Trail

View details for race Running with the Herd 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

Wekiva Parkway 5K

Apopka, FL

Saturday, April 3rd, 2027

1 Mile

Trail

View details for race Wekiva Parkway 5K

Winter Park 50K, Marathon, Half, 10K & 5K – Mil...

Winter Park, FL

Saturday, May 29th, 2027

Ultra

Marathon

Half

Trail

View details for race Winter Park 50K, Marathon, Half, 10K & 5K – MileBuilt Cady Way Bridge Memorial Day 3-Day Challenge

AdventHealth Cool Sommer Mornings Triathlon-Dua...

Clermont, FL

Sunday, June 13th, 2027

Ultra

Trail

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

The Florida Run LEFTOVER Trail Race

Clermont, FL

Saturday, June 19th, 2027

Trail

View details for race The Florida Run LEFTOVER Trail Race

Independence Double (Two Days, Five Distances t...

Winter Park, FL

Saturday, June 26th, 2027

10K

Half

Trail

View details for race Independence Double (Two Days, Five Distances to choose from)

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

AdventHealth Cool Sommer Mornings Triathlon\Dua...

Clermont, FL

Sunday, July 11th, 2027

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 8th, 2027

Ultra

Trail

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

DeBary 50K, Marathon, Half, 10K & 5K – MileBuil...

DeBary, FL

Friday, September 3rd, 2027

Ultra

Marathon

Half

Trail

View details for race DeBary 50K, Marathon, Half, 10K & 5K – MileBuilt Gemini Springs Labor Day 4-Day Challenge

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

AdventHealth Cool Sommer Mornings Triathlon\Dua...

Clermont, FL

Sunday, September 12th, 2027

Ultra

Trail

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

Explore more in Winter Park, FL

Jump straight to races by distance, month, or type.

Distance

5K 10K Half Marathon Marathon

Month

November December January

Race type

Trail Boston Qualifiers Fast Courses

Run clubs

Run clubs in Winter Park

Race weather

Best months to race in Florida

Ranked