The Pilgrim Trail was first an Indian footpath, then it was used by the early settlers traveling between Plymouth, Duxbury, Marshfield and Scituate. It was known as the Green Harbor Path, and as an existing road it was incorporated into the court-ordered road in 1647. The entire record on the court order can be seen in Plymouth, (Old Colony Records, Vol. 1, Page 58), showing that on May 10, 1647 this was the first official road in Plymouth Colony and possibly in America.

In Marshfield lies the best preserved part of this highway, and it can be walked from its entry at the Duxbury line on Careswell Street, over Black Mount and right down what is the driveway of the Webster Estate. The part that went over Presidential Circle to Winslow Cemetery is no longer visible.

In no other town is this historic trail as visible as it is in Marshfield and this is due to the preservation efforts of the Historical Commission working with the Planning Board. Large portions of the Trail have been legally protected and the part that runs through the Webster Estate is crucial to the Pilgrim Trail Preservation Program.