Trail Running calendar near Jackson 2026-2027

A 5K on October 24, 2026 at Stratham Hill Park that runs along Great Bay and benefits Great Bay Stewards; the mostly downhill course includes a race shirt for timely registrants and a bib with a beer or cider coupon.

Holistic Hustle in Kennebunkport features a timed 5K, a trail 10K and a kids half mile fun run at Emmons Preserve on October 31, 2026. The community fundraiser includes music, family activities, finishers medals and a raffle.

A small community 2.5 mile trail run at Thorne Head Preserve on October 31, 2026, with river views, a fall breakfast, and proceeds supporting local trails.

A costumed, timed 5K trail run at Wells Reserve at Laudholm on October 31, 2026 that raises funds for coastal conservation and restoration.

Hugs From Vets Trail 10Kish in Henniker, New Hampshire on November 1 features a mixed trail and country road course and raises funds for American Legion Post 78. The field is limited to 150 participants and awards are given to overall and a..

Night-time trail races of 5k and 10k at Cranmore Resort on November 7, 2026, requiring headlamps and featuring reflective course markers and LED lighting.

A Last Person Standing mountain event with hourly 2.25 mile laps that climb about 1,209 feet each. Aid, hot food, camping, elevation milestone prizes, and awards are provided; conditions may include cold, snow, or ice.

Thanksgiving morning trail event in Jackson, NH featuring a trail 5k and a kids 1k fun run, with day-of registration and awards for top finishers.

Krampuslauf brings a Krampus-themed running event to Dartmouth Skiway in Lyme, New Hampshire, with 5K and 10K loops and a 9 hour 10K lap challenge. Finishers receive medals and lap runners collect pins and a 50K medal.

Two-day national snowshoe championships in Concord NH with 10K and 5K races, age-group awards, and fleece blankets for top finishers.

A July 4 community run in Lebanon NH offering 6.2 and 5K courses along the Mascoma River trails with on-site registration, bib pickup, parking and age-group awards.

Trail relay held in July at Ascutney Outdoor Center in Brownsville VT featuring multi-runner team divisions, single track trails, camping and glamping options.

A backyard ultra in Portland ME where runners repeat an approximately 4.16 mile mostly flat loop each hour until one runner remains.

A last runner and rucker standing event on a 1 mile loop at Northeast Slopes in Corinth VT, with weighted rucking rules and memorial loops honoring members of 2/4 Marines.