Trail Running calendar near Chesterfield 2026-2027

A five-race Monday evening cross country series at Wickham Park in Manchester CT, the 35th edition features roughly 2.4 to 2.6 mile courses, a discounted full-series entry, and proceeds supporting the Manchester High School Shoe Fund.

A trail relay in Mine Falls with a dressed rubber duck as the baton, offering a two person 5 Mile relay and a two or three person 5K relay. Entry is free and donations support the Humane Society of Greater Nashua.

Notchview Ultra in Windsor, MA runs July 10 to 13, 2026 and offers multiple timed and distance events from 6 hours to 100.7 miles. The race uses a groomed 1.9 mile perimeter loop with an aid station and on-site amenities.

A 118-mile team trail relay on July 10-11, 2026 at Ascutney Outdoor Center in Brownsville, VT, featuring single-track trails, camping at Ragnar Village, glamping options for some teams, and village activities like bonfires and food trucks.

An annual trail race at Blueberry Hill Outdoor Center in Goshen, Vermont, offering 5 km and 10 km plus backcountry courses with forest scenery and a Hogback Mountain viewpoint; proceeds support trail maintenance.

A 50K trail ultramarathon made of five 10K singletrack loops through the Spaulding Academy grounds in Northfield NH, with on course aid, drop bags, and a strict eight hour cutoff for the final lap.

Experience a four part summer trail series at the Dublin School Outdoor Center. Run a scenic 5K loop featuring singletrack and rolling terrain while supporting local charities and community needs.

A two day ultra in West Windsor, Vermont offering 100 mile and 100 kilometer races. 100 mile entrants must meet qualifying time standards, and all entrants must complete eight hours of approved volunteer service or pay a $250 buy out by Jun..

A memorial 5K run and walk at Owen Bell Park in Dayville CT that raises funds for a scholarship for Killingly Ag-Ed seniors. The day includes a 5K, a walk, and a kids fun run on off-road paths with possible trip hazards.

Trail races in Hartford, Vermont, through the Hartford Town Forest and Conservation Area. Courses mix logging roads, packed trails, and single track, with a 5K mostly downhill and a 10K that earns Western NH series points.

A 12 hour loop run in Lawrence Woods, Medford, MA on July 18, 2026. The roughly four mile loop has minimal aid and space for participants to set up personal stations near the course.

A 1 mile out and back on the Farmington Canal Heritage Trail with a crushed gravel surface and hand timing. Held July 19, 2026 in East Granby in two waves with limited parking; proceeds benefit charities.

Two trail-focused races at Beartown State Forest in Great Barrington, MA: a 5-mile loop around Benedict Pond and a roughly 13.5-mile half with significant climbing and technical terrain. The event is cupless with limited parking and shuttle..

A July 25, 2026 event in Corinth VT featuring Last Runner Standing and Last Rucker Standing formats with repeated 1 mile loops, an Honor Lap that benefits Northeast Slopes, medals, and a 24th mile fast lap prize.

A trail race at Soapstone Mountain in Somers, CT featuring a 5.5 mile loop with six ascents, a cupless water stop, a 50 runner cap, and course sections that can be steep and rocky; organized by the Shenipsit Striders.

A roughly 3.8 mile trail race at Kingman Farm in Madbury, NH on July 26, 2026, featuring rolling nordic style paths and switchback singletrack; proceeds support the Doug Flutie Jr. Foundation for Autism and day of registration is available.

A 3.1 mile lap race at Chris Lewit Tennis Academy near Manchester, Vermont, held on wooded trails beside the West River. Net proceeds support veterans charities and all racers receive a free T shirt; family activities include river swimming..

A community trail run in Bedford, New Hampshire on July 30, 2026 featuring a 5 km course with age-based categories and fees, online registration with a noon deadline, and options to donate or buy merchandise to support the Rotary Club of Be..

A multi-day 75-mile stage race and a point-to-point 50K on the Sunapee Ragged Kearsarge Greenway featuring technical single-track, significant elevation gain, on-course aid stations and transported overnight gear, plus a $35,000 prize purse..

Trail races near Middlebury, Vermont offering 36 mile and 14 mile courses on mountain single track with substantial elevation gain and views from Mount Moosalamoo into Lake Dunmore.