Trail Running calendar near Westwood 2025-2026

The Cross-Connecticut Run for Mental Health Awareness is a unique 56-mile group running event held annually in Connecticut, starting in West Suffield and ending in New Haven along the scenic, flat Farmington Canal Heritage Trail. This non-competitive challenge supports Mental Health Connecticut thro..

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..

Run for the Hills is an annual 5K trail run and walk held at the Oswegatchie Hills Nature Preserve in Niantic, Connecticut. The event features a scenic course that winds around Clark Pond and through over 450 acres of coastal forest, offering participants a beautiful natural setting. It serves as a..

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 running event scheduled for September 14, 2025, in Westport, MA. Participants can enjoy a beautiful trail run through the vineyard, covering approximately 3 miles amidst picturesque farms and vines. After the race, attendees can indulge i..

The Pisgah Mountain Trail Races, held in Pisgah State Park, Chesterfield, New Hampshire, feature two trail running distances: 50K and 23K. Organized by the Red Clover Rovers, this event serves as a fundraiser for the New Hampshire Special Olympics, with all profits supporting their mission. The race..

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 Mt. A Trail Challenge is an annual running event taking place at Mount Agamenticus in York, Maine. Scheduled for September 20, 2025, the event features two courses: a 5K and a 1-mile challenge, allowing participants to run, hike, or stroll.The race is timed traditionally with stopwatches, and wh..

The Hooksett Kiwanis 5K Trail Race is an exciting running event taking place in Hooksett, NH, featuring a 5K race for all runners and walkers, as well as a Kid's Fun Run for children aged 12 and under. The race begins at Heads Pond trail and follows a scenic route through wooded conservation areas,..

The Bear Brook Trail Races, held in Allenstown, New Hampshire, showcase the scenic beauty of Bear Brook State Park with its single-track trails, steep hills, and blueberry fields. The event offers three distances: a 10K following "Mindy's Loop," a Half Marathon, and a Marathon, with marathoners runn..

Run for Nature in Lowell, MA, is a community-focused running event held at Shedd Park, featuring a 10K trail run, a 5K run/walk, and a 1-mile Kids Fun Run/Walk. The course winds through scenic trails in Shedd Park and Rogers Fort Hill Park, including a stretch along the Concord River Greenway, with..

The Run for the Pumpkins Trail Run is part of the WTAC Fall Race Series, taking place at Bradford Preserve in Westerly, Rhode Island. Scheduled for October 4, 2025, the event features a 10K, a 5K, and a children's 1K run for participants aged 10 and under. The courses showcase the natural beauty of..

The Aggie Ram Trail Run 5k will take place in Walpole on Sunday 5 October 2025. You can run between 5 and 5 kilometers.

The Groton Town Forest Trail Races will take place in Groton on Sunday 5 October 2025. You can run between 3 and 9 miles.

The Houghton's Pond Trail Races feature two distances: a 7-mile race and a 3.7-mile race, set in the scenic DCR Blue Hills Reservation in Milton, MA. Participants will navigate rolling dirt roads and forest paths, with elevation changes of approximately 700 feet for the 7-mile course and 300 feet fo..

The NipMuck Trail Marathon, held in Ashford, Connecticut, is a challenging 26.4-mile trail race along the scenic Nipmuck Trail. The course features diverse terrain including rocks, roots, mud, and wood bridges, with a route that heads south 6.2 miles to Route 44 and back, then north 7 miles to Bosto..

The Midstate Massive Ultra Trail is a challenging point-to-point ultra running event held in New Ipswich, New Hampshire, traversing the Appalachian Midstate Trail through central Massachusetts and crossing into New Hampshire, Rhode Island, and Connecticut. Scheduled for October 11-12, 2025, the race..

The Ghost Train Trail Races, held in Brookline, New Hampshire, is the state's original 30-hour ultramarathon event along the historic Granite Town Rail Trail. Participants can choose from multiple race distances including a 30-hour ultramarathon, a 30-hour 7-person relay, a 30-mile night race, a 15-..

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

The Tackle the Trail - Pomfret, CT will take place in Pomfret on Saturday 18 October 2025. You can run between 10 and 26 miles.