My father showed me the sign a while back, and it looks quite nice. It is labeled as "CONN. 69," and the sign itself is entirely made of wood, in which I would assume this is quite old. Below, is one picture of what the front looks like.

Also, what's interesting about the back is that, even though it is practically blank (painted green), there is an etching in the wood that reads "CONN HIGHWAY DEPT."

We're considering to sell the highway sign, since I lack an interest in it. Though before we do so, I am curious as to how old it is, not to mention if there is a general history behind this kind of highway sign that the state of Connecticut once used.