Trail Running calendar near Hillsborough 2026-2027

A run and walk along the Black River in Springfield, VT, offering 7.4K and 4K options to benefit Springfield High School Cross Country. In-person and virtual entries, packet pick-up, refreshments, prizes, and family registration pricing are..

Notchview Ultra runs July 10-13, 2026 at Notchview in Windsor, MA using a 1.9 mile loop with an aid station and bathrooms. Multiple timed and distance formats are offered, with campsite options and beneficiaries including local conservation..

Gather your team for a two day relay through the scenic Vermont countryside. Run flowy single track trails and camp under the stars at the Ascutney Outdoor Center for an unforgettable weekend of adventure.

A trail running event at Blueberry Hill Outdoor Center in Goshen, VT, offering 5 km and 10 km courses on marked trails and gravel roads, with post-race food, a raffle, awards, camping, and proceeds supporting local trail maintenance.

A technical 5.6-mile loop trail race in Northfield, NH, run over six laps with a ten-hour limit and about 4,400 feet of elevation gain; the event supports Spaulding Academy & Family Services and provides aid stations and drop bags each lap.

Run the TARC Blue Hills Skyline 12K on June 21 in Milton, MA, tackling about 2,300 feet of climbing on rocky, technical Skyline trails. Stair climbs and panoramic Boston skyline views make this a memorable trail challenge.

An annual July ultrarunning event in the southern Green Mountains offering 100 mile and 100 km courses with about 17,000 feet of climbing. The race includes a concurrent horse competition and raises funds for Vermont Adaptive Ski & Sport.

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 last-person-standing event in Corinth, VT with 1 mile loops and 300 feet of climbing for runners and ruckers, plus an Honor Lap that benefits Northeast Slopes; ruckers carry specified pack weights and medals are awarded at set milestones.

The Kingman Farm Trail Race is an old-school, show up and race event over 3.8 miles of rolling nordic paths and switchback singletrack. It benefits the Doug Flutie, Jr. Foundation for Autism. Day-of registration is available.

A three-day stage race around Lake Sunapee covering 75 miles with ~15,500 ft gain, plus a 50k option. The format includes overnight camping, organizer gear transport, stocked aid stations, mandatory safety gear, and a $30,000 prize purse.

Trail races in Goshen Vermont offer 36 mile and 14 mile options on mountain single track with significant climbing and views from Mount Moosalamoo. The event is family friendly and runs largely inside the Green Mountain National Forest.

Experience an obstacle course with over a dozen mud pits at the 508 INTL Adventure Sports Center. Enjoy a non competitive environment featuring music, food, and a festive atmosphere for both participants and spectators.

A 12 km trail race on August 1, 2026 in Hanover, NH, using Oak Hill XC and Trescott Trails with 1,446 ft of climbing. The event offers pre-registration and race-day entry with course support and timing services.

Experience the Trail Animals Running Club Summer Classic at Medfield's Noon Hill and Shattuck Reservations, a scenic and challenging 10 mile loop of forested singletrack that climbs to a Noon Hill vista. Distances include 10 miles, 40 miles..

A trail run and fundraiser in Poultney, Vermont featuring an 8K, a half marathon, and a kids fun run on wooded singletrack and double-track trails, cup-free aid stations, finisher awards, and post-race snacks and a raffle.

The 5K Race to the Ledges will take place in Concord on Saturday 8 August 2026. You can run 5 kilometers.

Trust Trail Fest offers 5k and 10k races on forest trails at the Kennebunkport Conservation Trust headquarters, followed by music, food, a beer tent and family activities. Proceeds support the Trust in Education programs.

Test your endurance in the White Mountains of New Hampshire with distances ranging from 20 to 100 miles. Navigate technical trails and significant elevation gains in this rugged mountain event starting from Waterville Valley.

Experience a scenic off-road trail run or walk through the conservation lands of White Barn Farm. This cup-less 5k event supports local sustainable agriculture and community food security in Wrentham.