Trail Running calendar near Winchester 2025-2026

The 2025 ACT Trail Fest, organized by the Arundel Conservation Trust, invites participants to run or walk through scenic trails in Arundel, Maine. This annual event features a 5k, 10k, and half marathon, showcasing the beautiful ACT Multi-Purpose Trail and Eastern Trails. All participants will recei..

The Hooksett Kiwanis 5K Trail Race is a community-focused running event taking place in Hooksett, NH. Participants can choose between a 5K race for all runners and walkers and a Kid's Fun Run, which is a half-mile course for children aged 12 and under. The race features a scenic route that begins at..

Run for Nature is a running event organized by the Lowell Parks and Conservation Trust, taking place at Shedd Park in Lowell, MA. Participants can choose from a 5K, 10K, or a Kids 1-Mile Fun Run. The event aims to support access to nature and educational programs, with all proceeds benefiting conser..

The Nipmuck Trail Marathon, taking place in Ashford, Connecticut, 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, i..

The Trust Trail Fest, organized by the Kennebunkport Conservation Trust, offers participants a choice between a 5k and 10k race on scenic forest trails at the Trust's headquarters. The event features a festive atmosphere with music, a beer tent, delicious food, and family-friendly games, creating a..

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 race options: 100 miles, 50 miles, and 30 miles. Set against the stunning backdrop of New England's autumn, participants will navigate the historic Midstate Trail, crossing thr..

The Mt. Tom Trail Race is an exciting running event set against the stunning backdrop of Mt. Tom, particularly during peak foliage.Participants can choose from a solo 25k, a 2-person 25k relay, or a solo 10k, all featuring challenging terrain and breathtaking views. The race supports the Kestrel Lan..

The Ghost Train Trail Races, taking place in Brookline, New Hampshire, is a unique running event that features a 30-hour ultramarathon, relay races, and shorter distances of 15 miles and 30 miles. Established in 2009, the event serves as a fundraiser for local conservation efforts, with all profits..

Womp Romp is an exciting running event taking place in Wompatuck State Park, Hingham, MA, featuring a 50K and a 10-mile race. Celebrating its fifth year, the event has consistently sold out, with a cap of 350 participants. The course includes a mix of single track, wide trails, and pavement, making..

The Powisset Farm Trail Run - Fall is a part of the Barn to Run Trail Race Series, taking place at Powisset Farm in Dover, MA. This event features four race distances: 8.3 miles, 5.6 miles, 3.1 miles, and 1.5 miles, catering to both experienced and novice trail runners. Participants can enjoy post-r..

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 will take place in Ipswich on Saturday 1 November 2025. You can run between 10 and 100 kilometers.

The Tarckey Trot 6 Hour - Winchester, MA will take place in Winchester on Saturday 15 November 2025.

The Li'l Rhody Runaround Trail Run is a popular running event taking place at Burlingame State Park in Charlestown, Rhode Island. Scheduled for November 16, 2025, participants can choose between two distances: an 8-mile and a 4-mile trail run. This event is part of the WTAC Fall Race Series, offerin..

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 TARC Winter Classic, organized by the Trail Animals Running Club, is a trail running event held at the Middlesex Fells Reservation in Stoneham, Massachusetts. Participants can choose from 8-mile, 32-mile, and 40-mile distance options, navigating a challenging course featuring roots, rocks, and e..

The TARCtic Frozen Yeti is an exciting trail running event organized by the Trail Animals Running Club, taking place at Hale Reservation in Westwood, Massachusetts. Scheduled for February 7-8, 2026, participants can choose between a 30-hour race or a 15-mile distance. The course features three loops..