Trail Running calendar near Winchendon 2025-2026

Ocean State Ultra is an endurance running event held at Big River State Management Area in West Greenwich, Rhode Island. The race offers three categories: a 100-mile ultra, a 12-hour, and a 6-hour race, all starting on the same day. The course features 10-mile loops combining 1.5 miles of desert, 1..

The Soapstone Assault is a challenging approximately 5-mile trail race held at Soapstone Mountain, featuring a unique course that requires participants to climb the mountain six times. This event is designed for those seeking a rigorous hill workout, as runners navigate steep, rocky, and potentially..

The Kingman Farm Trail Race is a welcoming and challenging running event designed for participants of all skill levels. Spanning approximately 3.6 miles, the course features Nordic-style paths and switchback singletrack, making it an exciting experience for runners. This event is organized by acidot..

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 People's Forest 7-Mile Trail Run is an annual trail running event held in Barkhamsted, Connecticut. It features a challenging 7-mile course through scenic forest trails, offering runners a chance to experience natural beauty and varied terrain. The race is part of the USATF Connecticut Mountain..

Lover's Lane in Chester, Vermont, is a unique 6- or 12-hour running event featuring a 1.8-mile loop course with 280 feet of elevation gain and loss per lap. The trail combines single and double-track paths along with jeep trails, offering a moderately challenging terrain. The race starts and finishe..

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 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 Tarc Summer Classic is a trail running event held at Noon Hill Reservation in Medfield, Massachusetts, featuring multiple race distances including 10 miles, 50K, and 40 miles. The course is a scenic, mostly forested loop with undulating terrain, roots, rocks, and a notable viewpoint at Noon Hill..

The Shenipsit Striders 50th Fatass is a celebratory running event held at Crandall's Park Pavilion in Tolland, Connecticut. Marking the club's 50th anniversary, the event features an 8-hour window where participants run multiple 5K loops on a trail course starting and finishing at the pavilion. Runn..

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..

Greenbelt's Vineyard Hill Trail Run is an annual trail running event held in South Hamilton, Massachusetts, located on the scenic town line of Hamilton and Topsfield. The race offers 5K and 10K distances that challenge runners with a course featuring Vineyard Hill, sections of Bradley Palmer State P..

The Jug End Loop Ultra is a 6-hour ultra running event held at Jug End State Reservation in Egremont, Massachusetts. Participants run multiple laps of a scenic 4.2-mile course featuring woods, fields, and an apple orchard, with an elevation change of 830 feet per lap. The course includes uphill and..

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 TARC Fall Classic is a popular trail running event held at Great Brook Farm State Park in Carlisle, Massachusetts, offering a range of distances including 10K, half marathon, 20 mile, 50K, and 50 mile races, plus a Yeti Mischief Mile and a free youth fun run. The courses wind through scenic New..

The Cross-Connecticut Run for Mental Health Awareness is a unique 56-mile group running event held annually in Connecticut, traversing the state north to south along the scenic and flat Farmington Canal Heritage Trail. Starting in West Suffield and ending at New Haven harbor, the course passes throu..

The Wicked Mudder will take place in Southwick on Sunday 7 September 2025. You can run between 5 and 5 kilometers.

The Run to Fall 5K in Northwood, New Hampshire, is an annual cross-country trail race held at Coe-Brown Northwood Academy. Celebrating its 25th edition in 2025, the event features a 5K race on the NH Youth State Meet Course, a 2.5-mile trail walk, and USATF-sanctioned 3K youth races for different ag..

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..