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Trail Running Calendar near Hollywood 2025-2026

Explore the top trail runs near Hollywood for 2025-2026! We've gathered 61 exciting races in the area. Check out our detailed list below to find your next local race.

May 2025
May
26
Monday

Memorial Day Classic

5 km
June 2025
Jun
7
Saturday

305 Iguana Man Run

5 km
Jun
14
Saturday

Miami 50/50

Trail Run 50 mi
Jun
14
Saturday

Half Marathon at Brian Piccolo Sports Park

5 km 10 km 15 km 13 mi
Jun
14
Saturday

The Best Races - Key Biscayne

5 km 10 km 13 mi
Jun
15
Sunday

The Dad Joke 5k

5 km
Jun
21
Saturday

The Best Races - Key Biscayne

5 km 10 km 13 mi
Jun
28
Saturday

Freedom 10K

5 km 10 km
July 2025
Jul
5
Saturday

The Best Races - Key Biscayne

5 km 10 km 13 mi
Jul
6
Sunday

Independence Day Triathlon

Triathlon
Jul
12
Saturday

Half Marathon at Brian Piccolo Sports Park

5 km 10 km 15 km 13 mi
Jul
17
Thursday

Levis JCC Run, Sweat & Beers 5k

5 km
Jul
26
Saturday

Half Marathon at Pompano Community Park

5 km 10 km 13 mi
Jul
26
Saturday

FUN FIT 10K

5 km 10 km
Jul
26
Saturday

The Best Races - Key Biscayne

5 km 10 km 13 mi
Jul
27
Sunday

TriKB

Triathlon
Jul
27
Sunday

Key Biscayne Triathlon

Triathlon
August 2025
Aug
2
Saturday

The Best Races - Key Biscayne

5 km 10 km 13 mi
Aug
9
Saturday

Half Marathon at Brian Piccolo Sports Park

5 km 10 km 15 km 13 mi
Aug
16-19
Sa - Tu

The Funky Run

2 mi 5 mi
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