Trail Running calendar near Henniker 2026-2027

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 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 challenge in Pittsfield, VT, run on repeated *2-mile* loops with 970 feet of elevation gain per loop. Participants compete for most laps or to endure the full day; tickets start at $135.

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 single-day endurance walk in North Conway offering 7, 14, 21, or 28 miles on a 7-mile loop with varied trail terrain, optional rucking weights, timed results, and tiered awards within a 10-hour finish window.

A Spartan obstacle race weekend at Carter & Stevens Farm in Barre, MA, featuring a Sprint 5 km with 20 obstacles, a Super 10 km with 25 obstacles, and kids races. The farm venue includes mud, woods, rolling hills and a farm store.

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 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 well marked 5k trail run and walk in Rochester, Vermont, organized by Pierce Hall Community Center and Ridgeline Outdoor Collective, following single-track trails and local connectors around River Brook Park.

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.

Notchview Ultra in Windsor, MA runs July 10-13, 2026 on a 1.9 mile loop with multiple time and distance options, an aid station, campsite planning, event SWAG, and proceeds benefiting local organizations.

A multi day team relay at Ascutney Outdoor Center in Vermont featuring 118 miles of trail, single track and switchbacks, camping at Ragnar Village, and team options from two to eight runners with on site amenities and community activities.

A seasonal trail race at Blueberry Hill Outdoor Center on July 11 2026 offering 5 km and 10 km plus backcountry courses through forest and a Hogback Mountain viewpoint, with proceeds supporting local trail maintenance.

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 roughly six-mile uphill trail race to Loon Mountain’s North Peak with about 3,066 ft of climb, very steep sections including the one-kilometer Upper Walking Boss, two fluid stations, and over $20,000 in prize money.

A July ultramarathon in Vermont offering 100 mile and 100 kilometer options, featuring 17,000 feet of climbing over country roads and forested trails. Proceeds benefit Vermont Adaptive Ski & Sport and a concurrent horse race accompanies the..