Trail Running calendar near Westport 2025-2026

The Survival of the F.I.T.test - 30+ Hour Trail Ultra is a challenging endurance event held in Cumberland, Rhode Island. Participants can choose between two course options: a flat, fast 2.1-mile loop or a more rugged 4.2-mile trail loop used in previous years. The event offers multiple race formats..

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, held in Westerly, Rhode Island at Bradford Preserve, is part of the WTAC Fall Race Series. This event features 5K and 10K trail races, along with a free 1K children's run for ages 10 and under. The courses highlight preserved town land and the Woody Hill Managemen..

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 Houghton's Pond Trail Races take place in the scenic DCR Blue Hills Reservation in Milton, Massachusetts, just south of Boston. This event offers two trail race distances: 7 miles and 3.7 miles, both starting and finishing near the Houghton's Pond Visitor Center. The courses feature rolling terr..

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

The Weir River Farm Trail Race, held annually in Hingham, Massachusetts, offers runners three trail distances: 10 miles, 6 miles, and 3.4 miles. The race courses wind through the scenic trails of Weir River Farm, Whitney, and Thayer Woods, with the 10-mile route including additional loops in Wompatu..

Womp Romp is an annual trail running event held in Wompatuck State Park, Hingham, Massachusetts, featuring a 10-mile single loop and a 50K race consisting of three loops plus an additional mile. The course offers a mix of single track, wide trails, and some paved sections, suitable for both novice a..

The Grills Trail Run, hosted by the Westerly Track & Athletic Club, takes place at Grills Preserve in Westerly, Rhode Island. Scheduled for October 25, 2025, it features two race distances: a 10-mile and a 10K. Both courses start and finish at Grills Preserve, showcasing scenic trails with about 80%..

The Powisset Farm Trail Run - Fall is a scenic trail running event held at Powisset Farm in Dover, Massachusetts. Scheduled for October 26, 2025, it offers four race distances: 8.3, 5.6, 3.1, and 1.5 miles, traversing trails through Powisset Farm and the neighboring Noanet Woodlands. The course feat..

The TARC Stone Cat Trail Festival is a renowned trail running event held annually in Ipswich, Massachusetts, within Willowdale State Forest. Offering a variety of distances including 10K, half marathon, marathon, 50-mile, and 100K races, plus a free youth fun run, the festival features a challenging..

The TARCkey Trot is a unique 6-hour timed running event set on a scenic 5K loop at Wright Locke Farm in Winchester, MA. Participants can run as many loops as they wish within the time limit, navigating a course filled with natural terrain challenges. The event promotes community engagement, offering..

The Li'l Rhody Runaround Trail Run is held at Burlingame State Park in Charlestown, Rhode Island. It features two trail running events: an 8-mile and a 4-mile course, both winding around the scenic Watchaug Pond. This race is part of the WTAC Fall Trail Race Series, offering a 10% discount for parti..

The Baystate Dirty Dog Trail Run-Ruck-Walk 5k, held in Berkley, Massachusetts, is a rugged outdoor event honoring military personnel, first responders, and their K-9 companions. Participants can run, ruck with weighted packs, or walk a challenging 5k trail through scenic natural landscapes. The even..

The TARC Winter Classic is a trail running event held annually at Middlesex Fells Reservation in Stoneham, Massachusetts. It offers challenging distances of 8, 32, and 40 miles along the Skyline Trail, known for its technical terrain featuring roots, rocks, and elevation changes typical of New Engla..

The Mount Hood Nutcracker Challenge is an annual cross-country running event held in Melrose, Massachusetts, at the Mount Hood Golf Club. This unique 3.5-mile race features a challenging, hilly course that changes every year, incorporating fairways, paved cart paths, road crossings, and occasional w..

The TARCtic Frozen Yeti is a winter trail running event held at Hale Reservation in Westwood, Massachusetts. It offers two distance options: a 30-hour ultra and a 15-mile race. The course features three roughly 5-mile loops marked with colored ribbons and reflective tape, starting and finishing at P..

The Merrimack River Trail Race will take place in Andover on Saturday 11 April 2026. You can run between 10 and 10 miles.