Trail Running calendar near Greenfield 2025-2026

The Woodland Trail Series, hosted by Tri-Valley Front Runners, is a well-established trail running event held at West Hill Dam in Uxbridge, Massachusetts. Celebrating its 27th year, the series features three races on different dates in June, July, and August, with distances of approximately 5, 4.6,..

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 Ordination Rock Run is a family-friendly 5K fun run held annually on July 4th in Tamworth, New Hampshire, as part of the town's Independence Day celebrations. Organized by the Tamworth Outing Club, the point-to-point course starts at the historic Ordination Rock and finishes at Kenneth Brett Sch..

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 Spaulding Woods 50K is a challenging trail race held in Northfield, New Hampshire, featuring a technical 5.6-mile loop with rocks, roots, and footbridges. Runners complete six laps totaling approximately 34 miles with 4,400 feet of elevation gain, primarily on singletrack trails. The event suppo..

The Loon Mountain Race is a challenging mountain trail event held in Lincoln, New Hampshire, covering approximately 6.03 miles with a 3,066-foot elevation gain. The race ascends the slopes of Loon Mountain, featuring diverse terrain such as trails, grass ski slopes, and cat tracks. Notable for its s..

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 12 Hours of Lawrence Woods is a half-day ultrarunning event held in Medford, Massachusetts, within the scenic Lawrence Woods section of the Middlesex Fells Reservation. Participants run a roughly 5-mile loop course that stays within the woods without crossing over itself, sharing only one inters..

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 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 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 Waterville Valley, New Hampshire, within the White Mountain National Forest. It features three race distances: a grueling 108-mile 100-mile ultra with 29,000 feet of elevation gain, a 58-mile 50-mile race ascending over 16,000 fe..