Trail Running calendar near Pittsfield 2026-2027

We have found 107 Trailruns within 80 miles of Pittsfield. See below where and when you can find the races.

A multi distance trail event in the White Mountain National Forest near Waterville Valley, New Hampshire held August 14 to 16, 2026. Races include 100 mile, 50 mile and 20 mile routes with substantial elevation gain and mandatory mountain g..

A 4.61 mile trail race at Moody Park in Claremont NH featuring narrow single track, wet sections and a steep drop and climb at Gravity Cavity. The event is part of the Western NH Trail Running Series and benefits the local parks department.

A scenic trail 5K on Wanakee’s 227 acre site in the White Mountains and Lakes Region of New Hampshire, held during Wanakee Homecoming. Proceeds support a camp scholarship fund and facility improvements.

A family friendly 5K on the Webb Forest trails organized by Wilmot Learning Place, featuring a signed course, water stations, timing for runners, post-race recognition, and nearby parking with overflow at local fields.

A community run at Oxbow Riverfront Park on August 15, 2026 along the Lamoille Valley Rail Trail with a 1.5 mile turnaround, one aid station, post-race refreshments, and awards for top finishers.

A biannual mountain trail race around Mount Mansfield covering about 11 miles and 5,000 ft of gain, featuring steep technical climbs, exposed alpine terrain and a strict 70-runner field with time-based qualification and limited refunds.

Weekly trail races at Catamount Outdoor Family Center in Williston, VT, with 5 km, 2.5 km half lap, and a cubbies category for ages 5 and under. Events run rain or shine with a stated thunder and cancellation policy.

A trail ultramarathon at Prospect Acres Ranch where runners complete repeated 2.2 mile laps in 2, 4, or 8 hour formats. Field camping is available Friday evening and registration is $40 with proceeds supporting future events.

A weekly trail race series in Williston, VT offering 5 km and 2.5 km options with adult and youth categories, bib pickup and on-course water refill. Events run rain or shine and follow a posted thunder and cancellation policy.

A trail race weekend in Waterville Valley NH with a 50K ultra, 23K, 4 mile and 1 mile family fun run. Courses use single and double track, have cup less aid stations, and include finisher awards and podium prizes.

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.

A mountain fundraiser in Stowe on August 30, 2026, featuring a 4.3 mile climb to Mt Mansfield for runners, hikers, and cyclists, plus a kids run, team options, donations, and event merchandise supporting the Catamount Trail Association.

September 2026

A weekly trail running race at Catamount Outdoor Family Center in Williston, VT, offering 5 km and 2.5 km courses with adult and youth categories. Races run rain or shine and follow a clear thunder and bib policy.

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.

A 50K trail ultramarathon through the Wilcox Lake Wild Forest near Stony Creek, NY, following a lollipop route from Harrisburg Lake. It features two stocked aid stations, 3028 feet of elevation change, and requires experience verification v..

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.

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.

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.

Sep 19-20, 2026 in Killington, VT: Spartan obstacle races across steep, off-trail terrain in the Green Mountains. Events include Sprint 5 km, Beast 21 km, Ultra 50 km and kids races; tickets start from $29.

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