Westport

Trail Running Calendar near Westport 2026-2027

Explore the top trail runs near Westport 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.

November 2026

DNRT Trail Race

Dartmouth | 6 mi from Westport

Trail Run 5 km 10 mi

Trail races at Destruction Brook Woods on November 14, 2026 with a 10 mile course and a 5K walk or run plus post-race recovery services and refreshments.

Trail races at Destruction Brook Woods on November 14, 2026 with a 10 mile course and a 5K walk or run plus post-race recovery services and refreshments.

"I'd Rather Be Indoors"

Bristol | 12 mi from Westport

Trail Run 5 km

A 5K off-road run on the Mt Hope HS cross country course in Bristol with start and finish at Bristol Town Beach, with proceeds supporting Mt Hope HS indoor track.

A 5K off-road run on the Mt Hope HS cross country course in Bristol with start and finish at Bristol Town Beach, with proceeds supporting Mt Hope HS indoor track.

5K for KJ

Tisbury | 25 mi from Westport

Trail Run 5 km

A charity run and walk on Martha's Vineyard featuring a 5K through Manuel Corellus State Forest with proceeds supporting a cross country scholarship.

A charity run and walk on Martha's Vineyard featuring a 5K through Manuel Corellus State Forest with proceeds supporting a cross country scholarship.

May 2027

Cape Cod Trail Race

Falmouth | 24 mi from Westport

Trail Run 10 km 20 km 30 km

A trail race at Crane Wildlife Management Area on May 2, 2027 offering 10K, 20K, and 30K on 100% trails with aid stations and a cupless policy.

A trail race at Crane Wildlife Management Area on May 2, 2027 offering 10K, 20K, and 30K on 100% trails with aid stations and a cupless policy.