Trail Running calendar near Winchester 2025-2026

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 Anchor Down Ultra is a seaside ultra-marathon event held at Colt State Park in Bristol, Rhode Island. It features multiple timed race options including 6-hour, 12-hour, and 24-hour ultra-marathons. Known as "The Smallest State's Longest Races," this event has been recognized by Men's Health Maga..

The Tarc Summer Classic is a trail running event held at Noon Hill Reservation in Medfield, Massachusetts, featuring multiple race distances including 10 miles, 50K, and 40 miles. The course is a scenic, mostly forested loop with undulating terrain, roots, rocks, and a notable viewpoint at Noon Hill..

The Shenipsit Striders 50th Fatass is a celebratory running event held at Crandall's Park Pavilion in Tolland, Connecticut. Marking the club's 50th anniversary, the event features an 8-hour window where participants run multiple 5K loops on a trail course starting and finishing at the pavilion. Runn..

The Midstate Massive Course Preview is a pre-race recon run held in Spencer, Massachusetts, offering runners a chance to explore a 13.1-mile section of the Midstate Trail used in both the 50-mile and 100-mile races. The run covers the trail segment between Aid Stations 6 and 8, providing participant..

The GTA Challenge is a 10K trail race held in Greenfield, New Hampshire, organized by the Greenfield Trail Association to support local trail maintenance. The course features a mix of class 6 roads, double track, and single track trails with natural obstacles like rocks and roots, offering a challen..

The Watermelon Wobbler 5k is a fun, off-road trail run held at White Barn Farm in Wrentham, Massachusetts. This 5K race takes participants through scenic conservation land and farm property, featuring dirt and gravel paths with natural obstacles like rocks, roots, and elevation changes. Open to all..

Greenbelt's Vineyard Hill Trail Run is an annual trail running event held in South Hamilton, Massachusetts, located on the scenic town line of Hamilton and Topsfield. The race offers 5K and 10K distances that traverse Vineyard Hill, sections of Bradley Palmer State Park, the Bay Circuit Trail, and G..

The Old Goat Track Club XC Classic is a 5K cross-country race held at Water's Farm in Sutton, Massachusetts. Scheduled for August 24, 2025, it features separate Women's and Men's Open 5K races. The event serves as the first race in the USATF New England XC Grand Prix series and is part of the USATF..

The TARC Fall Classic is a popular trail running event held at Great Brook Farm State Park in Carlisle, Massachusetts, offering a range of distances including 10K, half marathon, 20 mile, 50K, and 50 mile races, plus a Yeti Mischief Mile and a free youth fun run. The courses wind through scenic New..

The Run to Fall 5K in Northwood, New Hampshire, is an annual cross-country trail race held at Coe-Brown Northwood Academy. Celebrating its 25th edition in 2025, the event features a 5K race on the NH Youth State Meet Course, a 2.5-mile trail walk, and USATF-sanctioned 3K youth races for different ag..

The PCS Harvest Hustle 5K & Kids Run is a community-focused event held at Pomfret Rec Park in Pomfret Center, Connecticut. It features a 5K trail run and a kids' fun run of half a mile, supporting the Pomfret Community School Parent Teacher Organization. The PTO uses funds raised to enhance educatio..

The Veterans Count Nashua 5k Fun Run & Walk will take place in Nashua on Sunday 14 September 2025. You can run between 5 and 5 kilometers.

The Wine Run at Westport Rivers Vineyard & Winery is a scenic trail running event held in Westport, Massachusetts. Scheduled for September 14, 2025, the race features a roughly 3-mile course winding through picturesque farms and vineyards. Participants enjoy a relaxed atmosphere with professional ti..

The Pisgah Mountain Trail Races, held in Pisgah State Park, Chesterfield, New Hampshire, feature two challenging distances: a 50K and a 23K trail run. Organized by the Red Clover Rovers, this event supports the New Hampshire Special Olympics, with all profits benefiting their mission. The races star..

The Gunstock 5K and Canicross 5K take place at Gunstock Mountain Resort in Gilford, NH, as part of the annual Food Truck Festival. The event features a 5K trail run and a Canicross 5K where participants run with their dogs, followed by a 100m fun run for children under five. The course is a loop aro..

The Hooksett Kiwanis 5K Trail Race, held in Hooksett, New Hampshire, is a scenic trail run starting at Heads Pond trail and finishing at the Hooksett Public Library. The course features a hard-packed stone dust surface and wooded conservation trails, offering a natural and enjoyable running experien..

The ACT Trail Fest, held in Arundel, Maine, is an annual trail running event organized by the Arundel Conservation Trust. Participants can choose from a 5k, 10k, or half marathon course that winds through the scenic ACT Multi-Purpose Trail and Eastern Trails, featuring beautiful woodland and stream..

The Bear Brook Trail Races take place in Bear Brook State Park, Allenstown, New Hampshire, offering a marathon, half marathon, and 10K race. The courses feature scenic single-track trails, steep climbs, and expansive blueberry fields, showcasing the park's natural beauty. The marathon consists of ru..