Trail Running calendar near Chester 2026-2027

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.

A 12 km trail run on the Oak Hill XC and Trescott Trails in Hanover, NH on August 1, 2026, featuring rolling singletrack, about 1,446 feet of climb and on-course support; pre and day of registration options are available.

A five mile trail race on the Gurney Lane Trails in Queensbury, NY featuring single track terrain, chip timed results, age group awards, a post race celebration and proceeds benefiting the Under the Woods Foundation.

A community fundraising day in Groton, MA on August 5, 2026 featuring an 8.4 mile three-person relay, kids single-loop race and Little Lambs mini runs, followed by barbecue and activities, with proceeds to six local charities.

An eight hour track event at Clapp Park in Pittsfield with a virtual option, chip timing, on course bottle drop aid, and age division awards. Proceeds support the AYJ Fund and several discount codes are available.

Trail run and fundraiser in Poultney Vermont featuring an 8K, a half marathon and a kids fun run on singletrack and double track trails. Cup free aid stations offer refills, with awards, snacks and a post race raffle.

Lover's Lane in Chester VT is a time-based trail running event on August 8, 2026, offering six or twelve hour options on a 1.8 mile loop with 280 ft elevation per lap. Basic aid and food are provided and proceeds support local organizations..

The 15th Annual 5k Race to the Ledges in Concord, NH on August 8, 2026 features a short road and trail course and includes post-race brunch boxes to take away. Registration includes an adult 5 km entry and a free kids 5 km for ages 6 and un..

A community 5 km run in Derry, New Hampshire on August 8, 2026, with adult and kids categories and online registration closing August 7, 2026.

Trail runs from Okemo's Jackson Gore area climb to the mountain summit and return on dirt roads and single track. Distances include a 7.6 mile 2500 vert race and a family run under one mile; registration includes shirt, lunch, and medal.

Multi-distance trail ultras in the White Mountain National Forest around Waterville Valley, NH, featuring long climbs, exposed ridgelines, mandatory mountain gear, and live split tracking for the 100, 50, and 20 mile courses.

A multi day timed trail event on a Winchendon farm using a roughly two mile loop. Runners choose from six hour day or night, 12 hour, 24 hour, or 48 hour formats under the Sturgeon Moon.

A 4.61 mile trail race at Moody Park in Claremont NH featuring narrow single track, wet sections and a steep drop and climb at Gravity Cavity. The event is part of the Western NH Trail Running Series and benefits the local parks department.

Wanakee Wilderness 5K on August 15, 2026 is a trail run across 227 acres of hills and woodland valleys in the White Mountains and Lakes Region of New Hampshire. Proceeds support the camp scholarship fund and the day includes a Homecoming BB..

A family friendly 5K on the Webb Forest trails organized by Wilmot Learning Place, featuring a signed course, water stations, timing for runners, post-race recognition, and nearby parking with overflow at local fields.

A 4 mile open time trial on the single track trails of Schenectady Central Park with individually timed laps. All proceeds go to Hive of Hope, a community organization supporting recovery through connection and movement.

A trail ultramarathon at Prospect Acres Ranch where runners complete repeated 2.2 mile laps in 2, 4, or 8 hour formats. Field camping is available Friday evening and registration is $40 with proceeds supporting future events.