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Trail Running Calendar near Barnstable 2026-2027

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Explore the top trail runs near Barnstable for 2026-2027! We've gathered 4 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

October 2026
Oct
11
Su

Clam Crawl

Trail Run 3 km 5 km
Beach fun run at Sandy Neck Beach with 3K and 5K options that raises funds for marine biology scholarships and local youth programs.
Oct
24
Sa

Relentless Run & Ruck Challenge

Trail Run 5 km 10 km
Timed trail challenge at Camp Greenough offering 5K, 10K or a six hour loop with run or ruck divisions and separate male and female rankings.
Oct
24
Sa

Sheriff's Meadow Foundation Trail Run

Trail Run 3 mi
Free trail run at Caroline Tuthill Preserve in Edgartown featuring a 3.1 mile loop through pitch pine forest, salt marsh and a 160 foot boardwalk.
Oct
31
Sa

Grumpy's Cranberry Harvest 5K

Trail Run 5 km
A 5K through the cranberry bogs at AD Makepeace in Wareham on October 31, 2026, with online registration open and awards for overall and age group finishers.
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