Trail Running calendar near Derry 2026-2027

A community run on a three-loop course at the Natick Community Organic Farm, mixing trail, field, and road surfaces. Participants receive a commemorative chicken medal and top finishers are tracked in adult and kid categories.

A 5.6 K trail run and walk at Berry Pond in Harold Parker State Forest on June 14, 2026. Walkers and leashed dogs are welcome; prizes are awarded, all entrants receive a bandana, and hotdogs are provided after the race.

Part of the Grit Series at Dublin Outdoor Center, this trail event offers a 10K and a half marathon over rugged trails with significant elevation gain and views of Mount Monadnock. Registration runs May 3 to June 6, 2026.

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 only 5K obstacle mud run at Kimball Farm in Haverhill on June 21, 2026. The course has 18 plus obstacles and is open to women aged 7 and up who may run, jog or walk.

A three-race summer trail series at West Hill Dam featuring well-marked wooded single and double-track trails, limited fields, age-group prizes, and a portion of fees donated to local food pantries.

A small weeknight trail race series around Portland Maine from June 25 to July 30 2026, featuring races of about 5K to 6.5 miles, capped fields, partnerships with local land trusts, and series prizes for those who complete three races.

Ultratrax Cranmore in North Conway, NH is a single day endurance walk on June 27, 2026 offering 7, 14, 21 and 28 mile loops with a 10 hour cutoff. The course follows forest singletrack and old ski trails with aid stations and timed results.

A Spartan obstacle weekend at Carter and Stevens Farm in Barre, MA on June 27 and 28, 2026 with Sprint, Super, and kids races, plus an obstacle workshop and spectator access.

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 community trail festival in East Bayside, Portland on June 28, 2026 featuring a 10K run, 15 or 30 mile bike rides, and a 2 Miler. Registration proceeds support Portland Trails and the Bicycle Coalition of Maine.

A fifteenth annual trail run in Webb Forest, Sunapee NH on June 28, 2026, covering about 4.5 miles to benefit the Sunapee Middle High School Track and Field program. The course features scenic single-track trails and a raffle of sponsor pri..

A family oriented 5k fun run in Tamworth, New Hampshire centered on historic Ordination Rock during July 4 celebrations. Organized by the Tamworth Outing Club, registration includes a bandana, ice cream, and a bib raffle entry.

A July Fourth run in Springfield VT along the Black River offering 7.4K and 4K distances plus virtual options, benefiting Springfield High School Cross Country. Family rates, on-site packet pick-up, and post-run refreshments are provided.

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.

A backyard ultra on Portlands Back Cove Trail where runners complete about 4.17 mile loops each hour until one runner remains. The mostly flat gravel course runs along a tidal estuary and includes staffed and unstaffed aid stations.

A looped trail 50K at Spaulding Academy in Northfield, NH featuring five 10K technical loops, about 32 miles and 4,000 feet of gain. Ten hour race limit, cupless format, and support for Spaulding Academy & Family Services.

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..

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.