Trail Running calendar near Pittsfield 2025-2026

The Jigger Johnson Ultras is a challenging trail running event held in Waterville Valley, New Hampshire, within the White Mountain National Forest. It features three race distances: a grueling 108-mile 100-mile ultra with 29,000 feet of elevation gain, a 58-mile 50-mile race ascending over 16,000 fe..

The GTA Challenge will take place in Greenfield on Saturday 16 August 2025.

The Webb Forest Wander is a family-friendly 5K race held in the scenic Webb Forest trail system in Wilmot, New Hampshire. Organized by the Wilmot Learning Place, a nonprofit preschool, the event offers a well-marked course through a beautiful nature preserve maintained by the New London Conservation..

The Aliza Lapierre Fan Club Trail Race, hosted by the Richmond Trail Running Club in Vermont, is a volunteer-run charity event promoting community and outdoor exploration. The race offers two distances: a challenging 50k covering about 8 miles of road and 23 miles of rugged trails with over 5,000 fe..

The Catamount Weekly Trail Running Race is a recurring event held at Catamount Outdoor Center, offering distances including a half lap, 5K, and 10K. The races take place rain or shine, with a clear thunder policy in place for safety. Participants receive new bib numbers each week to ensure accurate..

The Delta Dental Race To The Top Of Vermont is an annual event held every August, attracting hikers, bikers, and runners from across the U.S. and Canada to conquer Mt. Mansfield, the highest peak in Vermont.The challenging 4.3-mile course ascends the historic Mansfield Toll Road, featuring a steep e..

The Triple Dam 10K is a scenic running and walking event held at the Power Dam Recreation Area in Perkinsville, Vermont. The course is a beautiful loop featuring gently rolling terrain on a mix of grassy trails, dirt roads, and single track, primarily on the west side of the Black River and North Sp..

The Catamount Weekly Trail Running Race is a recurring event held at Catamount Outdoor Center, offering distances including a half lap, 5K, and 10K. The races take place rain or shine, with a clear thunder policy in place for safety. Participants receive new bib numbers each week to ensure accurate..

The Black Bear Trail Races, hosted by White Mountain Endurance in Waterville Valley, New Hampshire, offer a challenging and scenic trail running experience. The event features four distances: a demanding 50K with 7,700 feet of elevation gain over iconic 4,000-foot peaks, a 23K course on the oldest m..

The Catamount Weekly Trail Running Race is a recurring event held at Catamount Outdoor Center, offering distances including a half lap, 5K, and 10K. The races take place rain or shine, with a clear thunder policy in place for safety. Participants receive new bib numbers each week to ensure accurate..

The Groton Forest Trail Run, held in Groton, Vermont at Boulder Beach State Park, offers scenic and challenging trail races. In 2025, the event features two distances: a 15-mile race and a 6.2-mile race. Recently taken over by Onion River Outdoors, a Montpelier-based gear shop and community organize..

The NCVRC Run for Hope will take place in Morrisville on Saturday 13 September 2025.

Wilcox Wild is a challenging 50K trail ultra run held in the Adirondack Park Wilderness, New York, starting and finishing at Harrisburg Lake. The race course features rugged trails through the Wilcox Lake Wild Forest, passing landmarks such as Hope Falls, East Stony Creek Trail, Murphy Trail, Willis..

The Mountain Goat Cabin Trail Run takes place at the Merck Forest and Farmland Center in Rupert, Vermont. The main event features a challenging 7-mile loop with approximately 1,500 feet of elevation gain, winding through scenic trails and forest roads. Runners experience two historic cabins, Ned's P..

The Gunstock 5K and Canicross 5K take place at Gunstock Mountain Resort in Gilford, NH, as part of the 3rd annual Food Truck Festival. The event features a 5K trail run and a Canicross 5K where participants run with their dogs on a loop course of gravel roads and cross-country ski trails with rollin..

The Pisgah Mountain Trail Races, held in Pisgah State Park, Chesterfield, New Hampshire, feature two challenging trail distances: a 50K and a 23K. Organized by the Red Clover Rovers, this event supports the New Hampshire Special Olympics, with all profits benefiting their mission. The races start fr..

The Paine Mountain Anchor Challenge Trail Race, held in Northfield, Vermont, is a scenic and challenging 6K trail race that starts and finishes at the Norwich Shaw Outdoor Center. The course features a mix of gravel roads, single-track switchback trails, and steep descents, leading runners to the su..

The TAM Trek is an annual trail race and fun run held in Middlebury, Vermont, designed to support the Trail Around Middlebury (TAM), a scenic 19-mile footpath encircling the village and connecting conserved lands, schools, and local landmarks across Middlebury, Cornwall, New Haven, and Weybridge. Th..

The Royal (multi) Mile Hill Run is a 5K trail race held in Lincoln, New Hampshire, as part of the 50th Annual NH Highland Games & Festival. The challenging course features 800 feet of elevation gain across dirt trails, service roads, and ski trails at Loon Mountain. Participants receive a race shirt..

The Vermont 50 Ultra Run is an annual endurance event held at Ascutney Outdoors in West Windsor, Vermont, typically on the last weekend of September. Established in 1993, it features a challenging and scenic course through Vermont’s landscape. The event offers multiple race options including a 50-mi..