I an agree with this to an extent, but then you have most of Medford, Malden, and Everett which are very urban but just outside the ring. In those cases it's more like Route 60. It kind of switches over right around Medford Center, so that to the South/West it's more more 16 as the ring, including by Alewife (what I refer to as "edge city"). However, it also isn't really a "ring" at all as it cuts to the west through Arlington, Newton, and outside 95.
I think from the point of view of Winchester though, I can 100% see where you're coming from.
Oh yeah PS, I absolutely hate actually driving on Route 16!