Trail Running calendar near Roxbury 2026-2027

Teams are driven blindfolded several miles to an unknown location, then must navigate back to the start by the shortest route. This free team event uses cross country scoring and prohibits GPS, phones, and running on I 95 or I 495.

The Women+'s Morning Run in the Fells will take place in Winchester on Thursday 18 June 2026. You can run 3 miles.

A trail race at the Dublin School Outdoor Center on June 20, 2026 offering a 10K and a half marathon with significant elevation gain, rugged terrain, and views of Mount Monadnock.

A trail half marathon in Lynn Woods Reservation on June 21, 2026, run as three identical loops over forested singletrack and carriage roads. The event emphasizes environmental stewardship and uses a centralized start and finish at the main..

Muddy Princess Boston is a women-focused 5K obstacle mud run at Kimball Farm in Haverhill, MA on June 21, 2026. The event features muddy obstacles, hydration and rinse stations, participant items and a partnership with the National Breast C..

TSR Trail Race is a loop-format trail run on June 21, 2026, in Adams, MA, featuring hand and machine built singletrack with climbs, descents, and a gravel meadow loop; proceeds support Thunderbolt Ski Runners' trail stewardship.

A five‑race 5K trail series at Camp Saratoga across summer Mondays, capped at 375 entries for the series. Individual races or a full series package are available and proceeds benefit the Wilton Wildlife Preserve & Park.

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.

Spartan H3X is a staged Hurricane Heat endurance challenge at Riverside Farm in Pittsfield, VT on June 26-27, 2026. Participants choose 4 hour, 12 hour or 24 hour options and may continue through all stages up to 24 hours.

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.

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 5 mile loop run at the Cumberland Monastery with options to turn back early or add miles after the loop. The meeting point is behind the senior center where two trails join at the dirt parking lot and parking is ample.

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.