Trail Running calendar near Hillsborough 2026-2027

Three summer trail races at West Hill Dam in Uxbridge, MA, with well-marked wooded single and double-track courses, limited fields, age-group prizes, and a portion of fees donated to local food pantries.

A 72-hour endurance race in Pittsfield Vermont on June 26-28 2026 combining physical obstacles, navigation, and mental challenges. Tickets for the Death Race require a promo code issued after acceptance by the race director.

A three-stage Hurricane Heat endurance event at Riverside Farm on June 26-27, 2026, offering 4, 12, and 24 hour tiers that together form a full 24-hour challenge; entry is 18+ with 40+ challenges and team registration options.

A 24 hour endurance event in Pittsfield, Vermont on June 27 to 28, 2026. Runners repeat a two mile loop with 970 feet of elevation gain as they compete for most laps or aim to last the full 24 hours.

A mountain trail race in Killington, Vermont on June 27, 2026 covering 8.2 miles and 3,010 ft of gain with summits of resort peaks. The course features two aid stations, a steep Needle's Eye finish and a 700 runner cap.

UltraTrax Cranmore is a single day endurance walk in North Conway where participants choose 7, 14, 21 or 28 miles to complete within 10 hours. Options include carrying 10, 20 or 35 pounds and earning a Grey Wolf medal at higher levels.

A weekend of Spartan obstacle races at Carter and Stevens Farm in Barre MA featuring a 5 km Sprint with 20 obstacles and a 10 km Super with 25 obstacles. The program also includes a kids race and an obstacle workshop.

Team-based charity challenge in Bristol, NH on June 27, 2026 where teams of 6 to 12 complete Special Forces style stations at Recruit or Operator levels while fundraising supports veterans and first responders.

A roughly 4.5 mile trail run in Webb Forest near Sunapee, New Hampshire on June 28, 2026, benefiting the Sunapee Middle High School Track and Field program. The course features mountain vistas, single track and varied terrain, with raffle p..

A marked 5 km trail run and walk on July 4, 2026, starting and finishing at River Brook Park in Rochester VT. Online and same day registration are available; adult and kids categories include small prize certificates.

A community 5K in Tamworth on July 4, 2026 that runs from Ordination Rock to Kenneth Brett School over village streets and trails. Entry includes a commemorative gift, ice cream, and a bib raffle while youth under 18 run free.

Fourth annual July 4 event in Springfield VT with a 7.4K run and 4K walk along the Black River. Individual fee $20 and a $50 family entry for up to four people; in-person family pricing required.

Notchview Ultra is a multi day running event July 10-13, 2026 in Windsor, MA featuring fixed distance and timed races on a 1.9 mile loop with an aid station, camping logistics, and charity fundraising.

Trail relay at Ascutney Outdoor Center in Brownsville, VT on July 10-11, 2026 featuring 118 miles of single track, switchbacks and riverside trails; team options include Standard, Ultra and Black Loop with camping and glamping available.

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 made of five 10K loops on technical forest singletrack near Northfield, New Hampshire. The limited field and looped format bring runners back to aid and the start area each lap while navigating rocks, roots, and steady elevation chang..

A 12K trail race on the Blue Hills Skyline Trail with about 2,300 feet of climbing, rocky steep terrain, and minimal aid. The route follows Skyline blazes from the Blue Hills Ski Area parking lot and requires participants to carry hydration..

An uphill mountain trail race to Loon Mountain North Peak in Lincoln, New Hampshire, roughly 6.03 miles with about 3,066 ft of gain and sections up to a 40 percent grade, featuring over $20,000 in prize money.

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..

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.