Edgartown

Trail Running Calendar near Edgartown 2026-2027

Explore the top trail runs near Edgartown 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

Clam Crawl

Barnstable | 24 mi from Edgartown

Trail Run 3 km 7 km

Clam Crawl in Barnstable MA on October 11 2026 offers 3 km and 7 km race options, funds three marine biology scholarships, and supports Cape Cod Roller Derby’s youth skating scholarship program. Entry is limited to 100 with online registration closin..

Clam Crawl in Barnstable MA on October 11 2026 offers 3 km and 7 km race options, funds three marine biology scholarships, and supports Cape Cod Roller Derby’s youth skating scholarship program. Entry is limited to 100 with online registration closin..

Relentless Run & Ruck Challenge

Yarmouth | 25 mi from Edgartown

Trail Run 5 km 10 km

Trail endurance event at Camp Greenough offering 5K, 10K, and a 6 hour loop challenge with separate run and ruck divisions.

Trail endurance event at Camp Greenough offering 5K, 10K, and a 6 hour loop challenge with separate run and ruck divisions.

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.

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.

Grumpy's Cranberry Harvest 5K

Wareham | 28 mi from Edgartown

Trail Run 5 km

A 14th annual community 5K in Wareham, MA on October 31, 2026 held at AD Makepeace with adult and youth registration categories and published fees.

A 14th annual community 5K in Wareham, MA on October 31, 2026 held at AD Makepeace with adult and youth registration categories and published fees.