Trail Running calendar near Rupert 2025-2026

The Vermont 100 Endurance Race, held annually in July in Vermont, is one of America's oldest 100-mile ultramarathons and part of the Grand Slam of Ultrarunning. The race features a challenging course with 17,000 feet of climbing over country roads, forest trails, and scenic views of the southern Gre..

The Moosalamoo Ultra is a popular trail running event held in Goshen, Vermont, starting and finishing at the scenic Blueberry Hill Inn near Middlebury. 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 f..

The Barre Heritage Trail 5K is a scenic trail running event held in Websterville, Vermont, at the Barre Town Forest Trails near historic granite quarries. The 5-kilometer course features a mix of wooded single and double track trails with rocky and root-filled terrain, offering beautiful views and a..

The Wakely Dam Ultra is a challenging 55K ultramarathon held in Piseco, New York, within the Adirondack Park wilderness. The race follows a remote, technical trail along the Northville Placid Trail between Piseco Lake and Wakely Dam, featuring 3,300 feet of elevation gain. It is a self-supported eve..

The Magnificent Bastards Challenge, held in Corinth, Vermont, is a unique endurance event honoring fallen Marines from the 2nd Battalion 4th 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..

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 Landis Arboretum 5K Forest Run, held in Esperance, NY, is a scenic cross-country race through the arboretum’s forests and meadows, offering beautiful views of the Schoharie Valley. This rolling 5K course is part of the Route 20 Challenge Series and is USATF sanctioned. The event features chip ti..

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 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 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 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 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 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 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..

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