The Housatonic Railroad is interesting because it has two histories. It predates the New Haven RR as a short line whose main trackage ran north and south along the Housatonic River Valley, in CT and MA. It became part of the NHRR for many years, then reemerged as an independent when the NHRR became part of Penn Central. Today, the "new" Housatonic is a thriving freight short-line.
Have never been east of the Mississippi. But if I ever made it, this is one area I'd like to explore. Photos I've seen of the depot at Lee, being a depot fan, have me wanting to visit. Does it still stand? Boxcab E50
I will have to check that out next time I am up into MA. If it is still there I will try to get a picture or two.