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Trail Running Calendar near Winter Park 2025-2026

Explore the top trail runs near Winter Park for 2025-2026! We've gathered 125 exciting races in the area. Check out our detailed list below to find your next local race.

January 2026
Jan
31
Saturday

Me Strong

5 km
February 2026
Feb
3
Tuesday

Health in Action 5K

5 km
Feb
7
Saturday

Run for the Cherubs 5K

5 km
Feb
7
Saturday

Super Bowl Duathlon

Duathlon
Feb
14
Saturday

For the Love of Chocolate 5K

5 km
Feb
15
Sunday

Lake Apopka Scenic Trail

Trail Run 5 km 8 mi 30 km
Feb
20-21
Fr - Sa

Florida ANVIL Ultra Triathlon

Triathlon
Feb
21
Saturday

Real Florida 10K

Trail Run 5 km 10 km
Feb
28
Saturday

Inua 5k Run

5 km
March 2026
Mar
7
Saturday

Shamrock Shuffle - Clermont

5 km 10 km
Mar
7
Saturday

Best Damn Race Orlando

5 km 10 km 15 km 21 km
Mar
7
Saturday

OCBA Law Day 5K

5 km
Mar
8
Sunday

Great Clermont Triathlon

Triathlon
Mar
15
Sunday

Lucky Charm 5K

5 km
Mar
21
Saturday

The Spring Rising

5 km 10 km
Mar
21
Saturday

Amazing Race For Charity

3 mi
Mar
22
Sunday

AdventHealth Lake Minneola Half Marathon

3 mi 6 mi 13 mi
April 2026
Apr
4
Saturday

Grand Living Park at Lake Mary 5k Fun Run and Walk

5 km
Apr
4
Saturday

Dream Finders Homes Hippity Hop 5K

5 km
Apr
12
Sunday

The Great American Bacon Race - Orlando

5 km
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