Trail Running calendar near Milton 2025-2026

The Drummer Hill Trail Races, taking place in Keene, NH, offers a variety of race distances including 50K, 37.5K, 25K, and 12.5K. Participants can choose how many laps of the 12.5K course they wish to complete, allowing for a flexible and personalized racing experience. The course features technical..

The Wine Run at Sakonnet Vineyard is a unique running event scheduled for June 7, 2025, in Little Compton, Rhode Island. Participants can enjoy a scenic 3-mile trail run through the vineyard, concluding with a festive gathering featuring dinner, wine, and live music. Each runner will receive a souve..

The Nipmuck South Trail Race is a scenic 15.7-mile out-and-back race held at Mansfield Hollow State Park in Mansfield, CT. Participants will enjoy a beautiful course that follows the Fenton River, featuring varied terrain, small bridge crossings, and a climb to a 50-foot cliff. The event includes th..

The Summer Solstice Trail Run is an exciting early morning event held in Gay City State Park, offering participants three race distances: 3 miles, 5 miles, and 8 miles. The 8-mile race is part of the 2025 Blue-Blazed Trail Running Series and the USATF-CT Mountain, Ultra and Trail series, providing a..

The 7-11 Slurpee Day Ultra 60k is a unique running event taking place on July 11, 2025, in Connecticut. Participants will cover a self-supported distance of 37.5 miles, stopping at various 7-11 locations along the route. The event encourages a fun and relaxed atmosphere, with no strict course or pac..

The Soapstone Assault is a challenging trail running event that takes place around Soapstone Mountain, covering approximately 5 miles. Participants will tackle a rigorous course that requires them to ascend the mountain six times, making it a demanding hill workout. The race features steep, rocky, a..

The Stonington Cross Country 5K is a running event scheduled for August 13, 2025, in Pawcatuck, Connecticut. This race features a 5K course and a Children's 1/2 Mile, catering to participants of all ages. The race begins on the track at Stonington High School, followed by a scenic route that include..

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 Wahaneeta Trail Run is a 5K trail race taking place in Westerly, Rhode Island, as part of the WTAC Fall Race Series. This event emphasizes a "no frills" approach, foregoing modern amenities like t-shirts and extensive awards to keep costs low and logistics simple. Participants can enjoy a classi..

The Wine Run at Westport Rivers Vineyard & Winery is a unique running event scheduled for September 14, 2025, in Westport, MA. Participants can enjoy a scenic 3-mile trail run through the vineyard, surrounded by beautiful farms and vines. After the race, attendees can indulge in dinner, wine, and li..

The Charlie Stavros Memorial Beach Run is a free, end-of-summer 3-mile running event held at Westerly Town Beach, Rhode Island. Organized by the Westerly Track Club and the Stavros family, the race features a scenic route that includes a 1.5-mile out-and-back course along the beach at low tide. This..

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

The Run for the Pumpkins Trail Run, organized by the Westerly Track & Athletic Club, is part of the WTAC Fall Race Series and will take place at Bradford Preserve in Westerly, Rhode Island. This event features a 10K, a 5K, and a children's 1K run for participants aged 10 and under. The courses showc..

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 Grills Trail Run, organized by the Westerly Track & Athletic Club, is part of the Fall Race Series and features both 10-mile and 10K races. Set in the scenic Grills Preserve in Westerly, Rhode Island, the event showcases beautiful trails, bridges, and riverfront areas, with a course comprising a..