I am a bit disappointed that Mass GIS doesn't show that many trails for the Commonwealth.
While the entire state view looks like this:
Even when you zoom in to the large open space lands in our area, you don't get that much more information:
So to get trail data for the area, you need to do a Google Search. You might find, for example, this site.http://www.americantrails.org/resources/statetrails/MAstate.html
And you might find buried in WWW land, this 2003 trail guide for the area. http://robertbristow.home.comcast.net/~robertbristow/userguideweb/guide.html