Trail Running Calendar Massachusetts 2025-2026

The Notchview Ultra is a multi-day ultrarunning event held in Windsor, Massachusetts, featuring a variety of race durations including 100.7 miles, 72 hours, 48 hours, 24 hours, 12 hours, and 6 hours. The course is a scenic, well-maintained 1.9-mile perimeter loop trail around Notchview, with aid sta..

The 12 Hours of Lawrence Woods is a half-day ultrarunning event held in Medford, Massachusetts, within the scenic Lawrence Woods section of the Middlesex Fells Reservation. Participants run a roughly 5-mile loop course that stays within the woods without crossing over itself, sharing only one inters..

The Sweltering Summer Ultra is an annual running event held at Clapp Park in Pittsfield, Massachusetts. The 13th edition features an 8-hour race on a certified 0.355-mile dirt and cinder track, with runners switching directions halfway through. Participants can run or walk as many laps as they choos..

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..

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 challenge runners with a course featuring Vineyard Hill, sections of Bradley Palmer State P..

The Jug End Loop Ultra is a 6-hour ultra running event held at Jug End State Reservation in Egremont, Massachusetts. Participants run multiple laps of a scenic 4.2-mile course featuring woods, fields, and an apple orchard, with an elevation change of 830 feet per lap. The course includes uphill and..

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 Wicked Mudder will take place in Southwick on Sunday 7 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. The approximately 3-mile course winds through beautiful farms and finishes among the vineyard’s grapevines. After the run, participants enjoy a festive atmosphere with dinner, wine, and..

Run for Nature in Lowell, MA, is a community-focused running event held at Shedd Park, featuring a 5K Run/Walk, a 10K Trail Run, and a Kids 1-Mile Fun Run/Walk. The course traverses scenic double- and single-track trails through Shedd Park and Rogers Fort Hill Park, including a stretch along the Con..

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 Groton Town Forest Trail Races, held in Groton, Massachusetts, offer two challenging trail running distances: 9.5 miles and 3.4 miles. The courses wind through the scenic Groton Town Forest, featuring well-marked paths with no road crossings, combining narrow dirt roads and single-lane trails fi..

The Mt. Tom Trail Race, held within Mt. Tom State Park in Massachusetts, offers runners a challenging experience amid stunning fall foliage.Participants can choose from a solo 25k race with 3,600 feet of elevation gain, a 2-person 25k relay, or a solo 10k, all on rugged single-track hiking trails. T..

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 at Wompatuck State Park in Hingham, Massachusetts, scheduled for October 25, 2025. The race offers two distances: a 10-mile single loop and a 50K consisting of three loops plus an additional mile. The course features a mix of single track, wide trails,..

The Book It for Books 10k is a charitable running event held at Lake Accotink Park in Springfield, Virginia. The race features a 10k course that combines mostly trail running with some paved sections, including out-and-back routes on both the north and south sides of the lake. It benefits Reading is..

The Powisset Farm Trail Run - Fall is a popular 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 scenic trails through Powisset Farm and the neighboring Noanet Woodlands. The rac..

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 Race for DFL is a unique "last runner standing" backyard ultra event held at Kenty’s Farm in Winchendon, Massachusetts. Participants run a 4.1666-mile loop every hour on the hour, continuing until only one runner remains. The course features a mix of terrain including grassy fields, trails, crus..