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Trail Running Calendar near Oakland 2025-2026

Explore the top trail runs near Oakland for 2025-2026! We've gathered 114 exciting races in the area. Check out our detailed list below to find your next local race.

March 2026
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
Apr
26
Sunday

The Chicken Run 5k

5 km
May 2026
May
2-3
Sa - Su

Sunshine Double

5 km 10 km ... 42 km 50 km
May
10
Sunday

Mother's Day 5K - Winter Garden

5 km
May
23
Saturday

Remember & Honor - Memorial Day 5k

5 km
September 2026
Sep
26
Saturday

Margaritaville Run Orlando 10K

5 km 10 km 21 km
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