Thanks to John and Linda Osgood, we now know of this ski area that operated in Andover. Here are the details:
"I learned a few details to Boston Hill this weekend at my folks house in North Andover, MA. The first rope tow on Boston Hill came from a place right next door called Claypit Hill. Phillips Academy of Andover purchases the tow tow on Claypit and put it on Boston where they eventually hired Bob Dunn to operate the area. So that is three different areas for this one little town."