The Sharon Trails booklet, pages 24-26, has descriptions of each section of the Massapoag Trail.

The area around the Massapoag trail was once the major industrial center for Sharon. The stream and lakes provided power for the many mills. The ruins along the trail are the old mills and dams. There is a large stone marker at the beginning of the trail at the Massapoag Circle. 

The Massapoag Trail runs mostly on Sharon Town Conservation land and can be accessed northerly via a trailhead between 18 and 20 Winslow Road. It runs south, crossing Billings Street, passing by Manns Pond, and further south until the Quincy Street and Pond Street intersection close to Beach Street and the Lake Massapoag Boat Launch. 

The AllTrails website has a description and map of a hike at Massapoag Trail.