Trail Running calendar near Rupert 2025-2026

The Taconic Crest Trail run, part of the Northeast Ultra 8 (NEU8) series, takes place in Williamstown, Massachusetts. This self-supported, non-competitive group run covers approximately 36 miles with an elevation gain of around 9,000 feet, culminating at Mount Greylock, the highest point in Massachu..

The Cirque Series - Killington is a challenging trail race held in Killington, Vermont, featuring an 8.7-mile course with 3,190 feet of elevation gain. The route starts at the base of the K-1 Gondola and includes summiting two of Killington Resort’s peaks, passing two others, and traversing rugged t..

The Rochester 5K Trail Run/Walk takes place at River Brook Park in Rochester, Vermont. The well-marked course features a scenic route starting and finishing at the park, crossing a bridge behind the fire station and winding through single-track trails such as Chantrea Field, Chanterea Hill, and the..

The Springfield Stars & Stripes 7.4K is an Independence Day fun run and walk held in Springfield, Vermont, starting and finishing at the Toonerville Trail trailhead. Participants can choose between a mostly flat 7.4K run or a 4K walk along the scenic Black River. The event benefits the Springfield H..

The F.I.T. Sun Mountain Challenge is an annual trail running event held at Bromley Mountain in Peru, Vermont. It offers three race distances: 5K, 10K, and a challenging 25K ultra.The course features beautiful mountain trails with gradual ascents and descents, including over 1,400 vertical feet per 3..

The Notchview Ultra is a multi-day ultrarunning event held in Windsor, Massachusetts, featuring a variety of race durations including 100.7 miles, 72 hours, 48 hours, 24 hours, 12 hours, and 6 hours. The course is a scenic, well-maintained 1.9-mile perimeter loop trail around Notchview, with aid sta..

The Goshen Gallop is an annual trail running event held at the Blueberry Hill Outdoor Center in Goshen, Vermont. Celebrating its 47th year, the race offers 5K and 10K distances along well-marked courses featuring rugged gravel roads and cross-country ski trails within the Moosalamoo National Recreat..

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 challenging course features 17,000 feet of climbing over country roads, forested trails, and scenic views of the southern Green Mountai..

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