Winchester

Trail Running Calendar near Winchester 2026-2027

Explore the top trail runs near Winchester for 2026-2027! We've gathered 42 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

June 2027

Jun

MammothMarch Boston

Hingham | 19 mi from Winchester

Trail Run

A 20 mile single-loop hike through Wompatuck State Park on June 5, 2027, with aid stations, a finisher medal and on site parking.

October 2027

Oct

The Next Loop Endurance Series - New England

Wrentham | 28 mi from Winchester

Trail Run 5 km 10 km ... Marathon 50 km

Test your endurance on a scenic 5K trail loop in Wrentham where you decide how far to go one hour at a time with distances ranging from 5K to 50K.