Trail Running calendar near Pittsfield 2026-2027

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-ascent fundraiser in Stowe, Vermont, celebrating its 20th year while supporting the Catamount Trail Association. Participants run, hike, or bike 4.3 miles up Mansfield Toll Road and a kids fun run is held near the base.

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 race in the Wilcox Lake Wild Forest near Stony Creek NY, featuring a lollipop route, about 3028 feet of elevation gain, on-course aid and water filtering. Entry requires prior experience, waitlist review and a 10.5 hour limit.

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 community races at Springfield Dam include a free kids 0.5 mile, a 1 mile Maniac Mile for ages 10 and up, and a scenic 3.1 mile course with trails, food vendors, and family activities.

Trail race at Boulder Beach State Park in Groton, VT on September 12, 2026. Organized by Onion River Outdoors, it offers 25K and 12K distances; limited cell service means bring cash or check for day of purchases.

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.

Vermont Spartan Event Weekend at Killington Ski Resort offers mountain obstacle races over varied terrain, including a 5 km Sprint, 21 km Beast, 50 km Ultra, kids races and spectator options.

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.

A scenic 5K and 2 Mile Fun Run Walk at Crown Point State Historic Site on September 19, 2026, featuring trails, roads, and fields and raising awareness about online safety through a collaboration with prevention partners.

TAM Trek is a trail race and fun run in Middlebury, Vermont supporting the Trail Around Middlebury. Events range from a full 19 mile route around the village to shorter trail races and a family friendly two mile run.

A 5K trail race at Loon Mountain on September 20, 2026, as part of the 51st NH Highland Games, with 800 ft of elevation gain across dirt trails, service roads and ski trails. Registration includes a race shirt and festival admission.

A community 5K in Hillsborough, NH on September 20, 2026, organized by the Hillsboro Fire Department. The off-road course may be uneven and strollers are not recommended; registration runs March 25 to September 19 with a $30 fee.

A one lap up and down mountain race in Waterville Valley, New Hampshire on September 20, 2026, part of the USATF-New England Mountain Racing Circuit. The course uses grassy ski slopes and gravel service roads and includes three aid stations..

An 8.5 mile trail loop at Merck Forest in Rupert, Vermont with about 1,800 ft of climbing, two aid stations, and a separate 0.75 mile kids loop. Field limits apply and all proceeds support Merck Forest & Farmland Center.

A one day mountain trail challenge visiting five peaks around Westmore, Vermont, covering roughly 26 miles and about 6,142 feet of ascent. Staffed water and aid stations appear along the route and morning shuttles run from NorthWoods campus..