Trail Running calendar near Chester 2025-2026

The Jigger Johnson Ultras is a challenging trail running event held in the White Mountain National Forest, Waterville Valley, New Hampshire. It features three race distances: 100 miles, 50 miles, and 20 miles, each traversing rugged, mountainous terrain with significant elevation gains—up to 29,000..

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 challenging distances: a 50k covering about 8 miles of road and 23 miles of rugged trails with over 5,000 fe..

The Midstate Massive Course Preview is a pre-race recon run held in Spencer, Massachusetts, offering runners a chance to explore a 13.1-mile section of the Midstate Trail used in both the 50-mile and 100-mile races. The run covers the trail segment between Aid Stations 6 and 8, providing participant..

The GTA Challenge is a 10K trail race held in Greenfield, New Hampshire, organized by the Greenfield Trail Association to support local trail maintenance. The course features a mix of class 6 roads, double track, and single track trails with natural obstacles like rocks and roots, offering a challen..

The Serenity on the Trails will take place in Schenectady on Saturday 16 August 2025. You can run 4 miles.

The Saratoga Community & Cross Country 5K Challenge is a running and walking event held at Pitney Meadows Community Farm in Saratoga Springs, NY. The event features a 5K Run/Walk and a free 5K Run/Walk for kids aged five and under. Participants can enjoy a lively atmosphere with music, a food truck,..

The Thacher Park Trail Running Festival, held annually at Thacher State Park in Voorheesville, NY, offers a scenic and challenging trail running experience. Participants can choose from four distances: 10K, half marathon (13.1 miles), marathon (26.2 miles), and an ultra 50K. The course features a sh..

The Triple Dam 10K is a scenic running and walking event held at the Power Dam Recreation Area in Perkinsville, Vermont. The course features a beautiful loop on gently rolling terrain, combining grassy trails, dirt roads, and single track paths along the Black River and North Springfield Reservoir...

The Black Bear Trail Races, hosted by White Mountain Endurance, take place in scenic Waterville Valley, New Hampshire. This trail running event offers multiple distances: a challenging 50K ultra with 7,700 feet of elevation gain around iconic 4,000-foot peaks, a classic 23K course through the oldest..

The Springfield Dam Run will take place in Springfield on Saturday 6 September 2025. You can run 3 miles.

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. The race is known for its beautiful forested course and strong community atmosphere. Recently ta..

The Run to Fall 5K is an annual cross-country race held at Coe-Brown Northwood Academy in Northwood, New Hampshire. Celebrating its 25th edition in 2025, the event features a 5K cross-country race, a 2.5-mile trail walk, and youth USATF 3K races for different age groups. A kids' fun run around the t..

Wilcox Wild is a challenging 50K trail ultra run held in the Adirondack Park Wilderness, New York, on September 13, 2025. The race features a rugged lollipop course starting and finishing at Harrisburg Lake, covering 31 miles with 3,028 feet of elevation gain and loss. Runners traverse scenic trails..

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 Lucy Mac 5K9 is a trail running event held at Ascutney Outdoors in Brownsville, Vermont. Scheduled for September 13, 2025, it features a timed 5K race and a 1-mile race option, welcoming runners, walkers, and dogs. The course offers a scenic Vermont adventure with handcrafted trails at the weste..

The Veterans Count Nashua 5k Fun Run & Walk will take place in Nashua on Sunday 14 September 2025. You can run between 5 and 5 kilometers.

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 serves as a fundraiser for the New Hampshire Special Olympics, with all profits supporting their mission...

The Gunstock 5K and Canicross 5K take place at Gunstock Mountain Resort in Gilford, NH, as part of the annual Food Truck Festival. The event features a 5K trail run and a Canicross 5K where participants run with their dogs, followed by a 100m fun run for children under five. The course is a loop aro..

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..