Trail Running calendar near Brattleboro 2026-2027

A loop-format trail run in Adams, MA, offering one to three loops and a separate 5 km meadow option on varied singletrack and hiking trails; proceeds support Thunderbolt Ski Runners trail stewardship around Greylock Glen and Mt. Greylock.

Five Monday evening 5K trail races at Town of Wilton Camp Saratoga across June to August 2026. Entries available per race or as a series package; 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.

An 8.2 mile mountain race in Killington, Vermont with 3,010 feet of ascent and a 700 runner cap. The counterclockwise course summits Killington Peak, includes two aid stations, marked trails, and a steep Needle's Eye finish.

A Spartan obstacle weekend at Carter and Stevens Farm in Barre Massachusetts featuring a 5 km Sprint, a 10 km Super, kids races, and an obstacle workshop across mud, woods, and rolling hills.

A charity team challenge on June 27, 2026 in Bristol, NH that recreates Special Forces mission tasks. Teams of 6–12 choose Operator or Recruit levels, with awards for top teams, MVPs, fundraising leaders, and participant milestones.

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 family friendly Independence Day event in Springfield VT offering a mostly flat 7.4K run and a 4K walk along the Black River. Family pricing is available and a $10 virtual option supports the local high school cross country team.

A five-race Monday evening cross country series at Wickham Park in Manchester CT, the 35th edition features roughly 2.4 to 2.6 mile courses, a discounted full-series entry, and proceeds supporting the Manchester High School Shoe Fund.

Notchview Ultra in Windsor Massachusetts offers multiple timed and distance events on a 1.9 mile loop with an on-course aid station and camping options. Proceeds support the Trustees of Reservations and Baypath Humane Society.

A weekend trail running event in Brownsville Vermont offering a 5 mile Yellow Loop plus timed 6 hour and 24 hour ultra options on technical singletrack and ski run terrain. Camping at Ragnar Village and on-site amenities are 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 looped trail ultramarathon in Northfield, NH on July 11, 2026, the Spaulding Woods 50K runs five 10K singletrack loops with aid stations, a ten hour finish limit, and an eight hour cutoff to start the final loop.

A July endurance event in Vermont offering a 100 mile and a 100 kilometer race with 17,000 feet of climbing, a concurrent horse endurance ride, and fundraising that benefits Vermont Adaptive Ski & Sport.

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.