Trail Running calendar near York Harbor 2026-2027

An annual October trail event on the Granite Town Rail Trail near Brookline and Milford, NH, offering distances from 7.5 miles to a 30-hour ultramarathon. Proceeds support local Conservation Commissions for trail maintenance.

Mountain trail race at Cranmore Mountain Resort in North Conway, NH, offering a 10K over two loops and a 5K single loop with substantial elevation gain and one aid station.

Join the Womp Romp at Wompatuck State Park for muddy, scenic trail loops through South Field with 10 Miler and 50K options and hearty aid stations. Proceeds support local charities for a fun, community focused fall run.

Celebrate community and fitness at the Holistic Hustle 5K and 10K at Emmons Preserve in Kennebunkport. Family friendly fun with music, treats, face painting and a wood burned finisher medal while supporting School Around Us.

TARC Stone Cat Trail Festival at Willowdale State Forest in Ipswich, MA offers distances from a cider donut mile and youth run to serious ultras up to 100K. Rugged 12.5 mile loops of roots, rocks and rolling terrain make for a scenic, chall..

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.