Trail Running calendar near Chester 2025-2026

The Moosalamoo Ultra is a popular trail running event held in Goshen, Vermont, starting and finishing at the scenic Blueberry Hill Inn. It offers two race distances: a challenging 36-mile ultra with over 5,000 feet of elevation gain, and a 14-mile "Heavy Half" featuring about 2,400 feet of climbing...

The Magnificent Bastards Challenge, held in Corinth, Vermont, is a grueling endurance event honoring fallen Marines. It features a Last Man Standing race with 1-mile loops that include 300 feet of climbing, each to be completed within 20 minutes, repeated until only one runner remains. A special fas..

The Barre Heritage Trail 5K is a scenic trail race held in Websterville, Vermont, through the historic Barre Granite Quarries. The course features primarily single-track trails with wooded, rocky terrain and many roots, offering a challenging and natural running experience. Walkers are welcome to pa..

The Ragged 75 Stage Race and 50K is a challenging trail running event held in Danbury, New Hampshire, centered around the scenic SRKG Greenway near Lake Sunapee. The 75-mile stage race spans three days, featuring steep climbs and technical single-track trails with about 15,500 feet of elevation gain..

The Nagdeo Lodge 15K Twilight Trail Run & Revelry is a scenic trail running event held in Chelsea, Vermont. Covering a distance of 15 kilometers, the race offers participants a unique twilight experience through natural terrain. The course is set around the Nagdeo Lodge area, providing runners with..

The Slate Valley Scramble, organized by Slate Valley Trails, is a trail running event taking place on August 9, 2025. Participants can choose between an 8k and a half marathon, both set on scenic singletrack and double-track trails in Vermont's Slate Valley. A Kid's Fun Run is also available for chi..

Lover's Lane in Chester, Vermont, is a unique 6- or 12-hour timed running event held on a challenging 1.8-mile loop featuring 280 feet of elevation gain and loss. The course combines single-track, double-track, and jeep trails, offering a fun and engaging experience for runners of all levels. The ev..

The Sweltering Summer Ultra is an annual running event held at Clapp Park in Pittsfield, Massachusetts. The 13th edition features an 8-hour race on a certified 0.355-mile dirt and cinder track, with runners switching directions halfway through. Participants can run or walk as many laps as they choos..

The Jigger Johnson Ultras is a challenging trail running event held in the White Mountain National Forest, starting and finishing in Waterville Valley, New Hampshire. It offers three race distances: 100 miles, 50 miles, and 20 miles, each featuring rugged, technical mountain terrain with significant..

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

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 and a 26k, both featuring rugged trails and road sections across Huntington, St..

The Thacher Park Trail Running Festival, established in 2014, takes place at Thacher State Park in Voorheesville, NY. This scenic event offers participants a choice of four race distances: 10K, 13.1M, 26.2M, and 50K, allowing runners to experience the park's beautiful trails. The festival promotes a..

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

The Groton Forest Trail Run, held at Boulder Beach State Park in Groton, Vermont, offers two challenging trail distances: a 15-mile and a 6.2-mile run. This event is designed to introduce participants to the scenic and rugged terrain of Groton Forest, featuring rocky and root-filled trails that test..

The Mountain Goat Cabin Trail Run will take place in Rupert on Saturday 13 September 2025. You can run 7 miles.

Wilcox Wild is a challenging 50K trail ultra held in the Adirondack Park Wilderness, New York, starting and finishing at Harrisburg Lake. The rugged course features a lollipop route passing through scenic areas including East Stony Creek Trail, Murphy Trail, Willis Lake, and Wilcox Lake, with an ele..

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 trail running distances: 50K and 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 race..

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..