Trail Running calendar near Medfield 2025-2026

Womp Romp is a trail race at Wompatuck State Park with scenic single track, wider trails, and some paved sections. Choose a 10 mile one loop or a three loop 50K and enjoy friendly aid stations and a community vibe supporting local charities..

Discover scenic single track trails at Grills Preserve in Westerly on October 24, 2026 with 10 mile and 10K options. Choose a distance and enjoy riverfront views and bridges as race two of the WTAC Fall Trail Race Series.

Celebrate fall trails at the TARC Stone Cat Trail Festival in Willowdale State Forest in November with distances from a fun Cider Donut Mile to a 100K. Run rugged single track on scenic loops while supporting local conservation groups.

TARC Winter Classic offers 8 32 and 40 mile trail races on the rugged Middlesex Fells Skyline Trail with roots, rocky climbs and occasional Boston skyline views. Affordable entry and proceeds support land conservation.