trainsinmaine wrote:This is a long shot, but there's a possibility that this location is not in Connecticut at all.
I located a postcard on eBay that depicts a section of the Rutland running through "Lion's Head" near Gassett, Vermont (in the Chester area). It's by no means identical to the above photo, but the topography is similar; I'm wondering whether it's facing in the opposite direction on a fairly long curve. Here's the link: http://www.ebay.com/sch/sis.html?_nkw=G ... 0568013637
This might solve the mystery of the "B" on the milepost: the mileage is indecipherable, the "B" could be Bellows Falls or (less likely) Burlington.
The mileage fits. But from looking at the Rutland postcard, it seems to me that "Lion's Head" is the rock formation directly above and to the left of the tracks, on the side of the cutting.
In the original postcard, on the other hand, it seems to me that "Lion's Head" refers to the rock formation up on top of the hill in the middle distance. That's what makes me wonder if the picture was taken on the Highland or the Naugy. Overhanging rocks and cliffs at or near the ridgeline is a common feature of the hills along both sides of the Naugatuck Valley.
Which leads me to a thought- wasn't the Meriden Branch (a/k/a Waterbury, Meriden & Connecticut River) part of the NY&NE, and thus the New England Railroad? Could this be somewhere along that? Location would be right for a postcard sold in Waterville.