Isaiah, I live in western Mass. yes the Berkshires fro Ct. up thru Mass. are areas where people have seen them, check out the BRFO site maps for the encounters.
Also the Ct. Mass. border in some area is remote and there have been sightings, as I am sure the Mass. Vt. and NH. borders may be active..
Used to live in CT, the Northwest part of the state (Kent, etc.) has had several recent sightings, Western MA also (same watershed) up through Williamstown. Not far from there to Whitehall NY which had a famous series of sightings some time ago. I would think the Appalachian Trail could be productive along with any of the national forest campsites….you kind of have to go explore and see if anybody is home…..though the usual “be careful what you wish for” warnings apply.