Trail Running calendar near Hamilton 2025-2026

Run the winding single lane trails of Groton Town Forest with a choice of 9.5 mile or 3.4 mile courses featuring roots, rocks and rolling climbs. Limited to 250 runners, this community race supports Groton trail maintenance and finishes wit..

Tackle the rugged NipMuck Trail Marathon in Ashford CT, a 26.4 mile trail test through rocks, roots, mud and wooden bridges. Run solo or as a two person relay and expect a challenging, hilly second half that rewards grit.

Hit the trails at the Keene Family YMCA Fall Foliage Trail Races in Keene, NH on Sunday, October 4, 2026, with 5K and 10K options through scenic fall woods. Enjoy chip timing, shirts for early registrants, and support local YMCA programs.

Tackle the Midstate Massive Ultra Trail, a UTMB Index point to point across New England following the historic Midstate Trail. Choose 100 mile, 50 mile or 50k routes through mountains, fields, roads and rivers for a multi state adventure.

Join the 20th Wayland / HFC Striders Cross Country Festival on October 11, 2026, featuring youth 3K races and open 5K events that support Wayland High School cross country and track. Presented by Middlesex Savings Bank with awards and commu..

Enjoy a scenic 3 mile trail at Sakonnet Vineyard, then celebrate with wine, dinner, music and a souvenir wine glass. BBQ only and kids BBQ options are available for those who prefer to skip the run.

Join a scenic trail run through NE Connecticut along the Air Line State Park Trail with marathon, half, 10K, relay and junior distances. Tackle the Trail supports local students pursuing higher education.

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.

Join a scenic 3.5 mile Thanksgiving trail run or walk around Scoville Reservoir in Wolcott CT on November 26, 2026 to benefit the Endometriosis Foundation of America. Enjoy post race yoga, finisher medals, swag and a dog friendly vibe.

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.