Trail Running calendar near Brattleboro 2026-2027

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 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..

Soapstone Assault is a 5.5 mile trail race in Somers, CT organized by Shenipsit Striders, featuring six ascents and about 1,500 feet of climbing. The course has steep, rocky sections, limited aid access, and the field is capped at 50 runner..

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 ultramarathon in Goshen, Vermont on August 1, 2026. Offers 36 mile and 14 mile courses on mountain single track with substantial elevation gain and views from Mount Moosalamoo.

A family-friendly mud run in Boston on August 1, 2026 featuring a **5K** course with obstacles, waist-deep mud pits, a pre-party and an after-party with music and food, plus value and VIP registration options.

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 7-mile USATF sanctioned trail race in Barkhamsted, CT on 08/01/2026. Registration runs 05/03/2026 to 07/31/2026 with a $20 fee and no race day registration; results posted online by Greystone Electronics.

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 race at Clapp Park in Pittsfield, MA on a certified .355 mile loop with chip timing, bottle drop aid, age group awards, and proceeds benefiting the AYJ Fund. A virtual option may be available.

A trail event at Noon Hill Reservation in Medfield offering a 10 mile loop plus 50K and 40 mile ultra options, mostly singletrack with roots, rocks, and a scenic Noon Hill vista; proceeds benefit The Trustees of Reservations.

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.

A timed 6 hour and 12 hour loop event in Chester, VT on August 8, 2026. The 1.8 mile loop has about 280 feet of climb per lap and basic aid plus communal food are available.

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..