Created in 2003 in honor of the Laurel Hill Association’s 150th Anniversary, the trail was named for Mary V. Flynn, the first woman President of the Association and the first woman on the Stockbridge Board of Selectman. The 1.2 mile trail was designed and built by Peter Jensen of Open Space Management, and follows the course of the old Berkshire Street Railway trolley line, which was in operation from 1902 to 1930. Old trolley trestle abutments can be seen on both sides of the Housatonic River, adjacent to the Goodrich Memorial footbridge that links Laurel Hill Park to the Mary Flynn Trail.
Beginning with a 100-foot long boardwalk, the flat, gravel trail runs east through a forest of birch, pine, and cottonwood, crosses over two wooden bridges, again meeting the Housatonic River. Along the way, remnant abutments are the only tangible evidence of an old swinging footbridge across the river, near a possible trolley stop that would have serviced Stockbridge’s East Main Street to the north. At the eastern-most end, the trail turns, narrows, and loops back alongside the river. It passes through embankments with vines and ferns and crosses two small bridges before rejoining the main trail.