Trail Running calendar near Roxbury 2026-2027

An inclusive trail festival at Northfield Mountain on August 29, 2026 that centers queer and trans runners and allies. It offers a 20k prediction race, an untimed 5k fun run or hike, and a Kid's Run with community-focused prizes.

A 10 km race at Power Dam Recreation Area in Perkinsville, VT on August 30, 2026, part of the Western NH Trail Running Series. Online registration closes August 28, 2026; youth entries are free and age-based fees apply.

Timed loop trails on Wachusett Mountain with 7, 14, 21, and 28 mile options over ski slopes and single-track. Participants have 10 hours to finish, with weighted vest options and marked courses; finishers receive a shirt and patch.

Trail Animals Running Club hosts a multi distance trail event at Great Brook Farm State Park on September 5, 2026. Looped 10K and 10 mile courses cover distances from 10K to 50 miles, plus a youth fun run and a Yeti Mischief Mile.

A community 5K run and walk in Nashua, NH on September 5, 2026 with free registration for veterans and children, a fee for participants 13 and older, event shirts, donation options and volunteer opportunities. Use #nashua5k for photos.

A lakeside trail run in Goshen, New Hampshire on September 5, 2026, with 3 mile and 5.7 mile courses, awards, swag, and a raffle. The longer distance awards points in the Western NH Trail Running Series.

Trail ultramarathon and half marathon in Bear Brook State Park near Allenstown, NH. The ultra varies between 50k and 100k and is navigated with GPX files only; aid stations do not provide cups.

An unsupported, end-to-end group run of about 56 miles along the Farmington Canal Heritage Trail from West Suffield to New Haven, organized as a fundraiser for Mental Health Connecticut with a 14 hour completion limit and required self-supp..

A Keene State College alumni cross-country meet on 09/12/2026 at the Keene State Athletic Complex featuring a men's 5K and a women's 2 Mile race; registration runs 09/06 to 09/12 with a $25 fee per event.

Thunder Run is a 5K trail race with more than 20 obstacles through woods and hills in Candia, New Hampshire on September 12, 2026. Organized by Raymond Area Rotary, 100% of proceeds support local and selected international projects.

Three events at the Springfield Dam on 09/12/2026 include a kids 0.5 mile, a one-mile Maniac Mile for ages 10+, and a 3.1 mile trail run with views of Mt. Ascutney. Food vendors and family activities are planned.

Trail races in Pittsfield State Forest on September 12, 2026 feature 50K, 25K, 15K and 5 mile options. The double loop course includes long climbs, fast descents and three aid stations, with proceeds supporting Free to Run.

Pisgah Mountain Trail Races in Chesterfield, NH offers 50k and 23k mountain trail ultraruns on Sunday 9/13/26. Aid stations provide LMNT, Tailwinds, and Untapped and proceeds support New Hampshire Special Olympics.

A USATF New England Cross Country Grand Prix meet at Great Brook Farm Ski Touring Center in Carlisle, MA on September 13, 2026, featuring a youth 2K and several 5K races across open and masters categories.

A weekend of Spartan obstacle races at Killington Ski Resort in the Green Mountains, featuring Sprint, Beast, Ultra and a Kids Race across steep, off-trail terrain. The event listing includes obstacle counts, sample pricing, and participant..

A community 5K trail race in Hooksett that runs from Heads Pond trail through wooded conservation land to the Hooksett Public Library. A separate 0.5 mile kids fun run is available and proceeds support local youth programs.

A community fundraiser in Pomfret Center with a trail 5K and a 0.5 mile kids run supporting the Pomfret Community School PTO. Early and later registration fees differ and awards plus finisher medals are given.

A community 5K in Jaffrey, NH offering a woods trail and a rail trail out and back. Proceeds support the volunteer Jaffrey Firefighters Company and equipment needs of the Jaffrey Fire Department.

An 18 mile out and back trail run from Windblown Ski Area toward Watatic Mountain Reservation, featuring steep, technical single track and uneven terrain. Prior trail running experience is strongly recommended.

Hope House 5K Trail Run and Walk for Recovery on September 19, 2026 at Schodack Town Park includes a 5K run or walk and a children's 1 mile fun run. Proceeds support Hope House services for people affected by substance use disorder.