Trail Running calendar near Winchendon 2025-2026

The Jug End Loop Ultra is an exciting running event scheduled for August 23, 2025, at Jug End State Reservation in Egremont, MA. Participants can engage in a 6-hour ultra event, completing as many laps as possible on a scenic 4.2-mile course that features a mix of uphill and downhill terrain. The ev..

The TARC Fall Classic, hosted by the Trail Animals Running Club, takes place at Great Brook Farm State Park in Carlisle, Massachusetts. This popular running event features a variety of distances, including 10K, half marathon, 20 miles, 50K, and 50 miles, along with a free youth fun run. The scenic c..

The Hooksett Kiwanis 5K Trail Race will take place in Hooksett on Saturday 20 September 2025. You can run 5 kilometers.

The Vermont 50 Ultra Run is an annual event held in West Windsor, Vermont, featuring a variety of races including a 50-mile ultra run, a 50K run, and several mountain biking options. Established in 1993, the event supports Vermont Adaptive Ski and Sports, promoting confidence and independence for in..

The Nipmuck Trail Marathon, taking place in Ashford, CT, is a challenging 26.4-mile race that showcases the rugged beauty of the Nipmuck Trail. Participants can choose between the full marathon or a relay option, where two runners split the course. The race features a variety of terrains, including ..

The Groton Town Forest Trail Races, organized by the Squannacook River Runners and Groton Trails Committee, feature two scenic courses of 9.5 miles and 3.4 miles through the picturesque Groton Town Forest. The trails are well-marked and consist of narrow dirt roads and winding paths, presenting a mi..

The Midstate Massive Ultra Trail is an endurance running event taking place in New Ipswich, NH, featuring three challenging races: 100 miles, 50 miles, and 30 miles. Set against the stunning backdrop of New England's autumn, participants will navigate the historic Midstate Trail, which crosses throu..

The Mt. Tom Trail Race, organized by Beast Coast Trail Running, offers participants a chance to explore the scenic beauty of Mt. Tom during peak foliage.The event features challenging courses, including a solo 25k, a 2-person relay, and a solo 10k, all set within the rugged terrain of Mt. Tom State ..

The Ghost Train Trail Races, taking place in October 2025, is New Hampshire's original 30-hour ultramarathon, featuring various race options including a 30-hour ultramarathon, a 30-hour relay, a haunted night 30-mile race, and 15-mile races. The event is held along the historic Granite Town Rail Tra..

The Womp Romp is an exciting trail running event taking place at Wompatuck State Park in Hingham, MA, featuring a 10-mile and a 50K race. This year marks the fifth edition of the event, which has consistently sold out, with a cap of 350 participants. The course includes a mix of single track, wide t..

The Hamsterwheel is an exciting ultrarunning event taking place in New Boston, NH, featuring races of 6, 12, 24, and 30 hours. Celebrating its 11th year, participants will run a scenic 4-mile loop along the New Boston Rail Trail, with opportunities for both individual and team entries. Runners can e..

The TARC Stone Cat Trail Festival, hosted by the Trail Animals Running Club, takes place at Willowdale State Forest in Ipswich, Massachusetts, offering a variety of race distances including 10K, half marathon, marathon, 50-mile, and 100K, along with a free youth fun run. Established in 2001, this ev..

The Baystate Dirty Dog Trail Run-Ruck-Walk 5k is a unique event taking place in Berkley, MA, designed to honor military personnel, first responders, and their K-9 companions. Participants can choose to run, ruck with weighted packs, or walk the rugged 5k trail, all while reflecting on the sacrifices..

The Krampuslauf is a unique running event held at the Dartmouth Skiway in Lyme, NH, featuring 5K, 10K, and a challenging 9-hour endurance race. Participants will navigate scenic mountain trails, starting at the ski lodge and tackling both Holt's and Winslow sides of the mountain. Runners can earn me..

The TARC Winter Classic, organized by the Trail Animals Running Club, takes place at the scenic Middlesex Fells Reservation in Stoneham, Massachusetts. This popular trail running event offers participants the choice of 8-mile, 32-mile, and 40-mile distances, showcasing a challenging course filled wi..