Connecticut has a Wine Trail and a Chocolate Trail and an Art Trail and a new Barn Trail (which I'm sort of excited about) and so many other trails that I lose track of them. So a Tiny Library Trail wouldn't be such a strange thing. From Pomfret to Windham, they are adorable. (And don't just take my word for it.) This picture of the one in Union is almost life-sized.
This one in Bethany is sort of an edge case. It probably wouldn't qualify, because there's a large modern library carefully concealed behind this front.
But on the other hand, these wreathed doors.
This one, in Naugatuck, is probably too much of a "real" library, and too large. But I'd include it, because it's pleasantly neoclassical and appears to be trying to hide behind these trees.
And because this literary detail - it goes all the way across - is too good to ignore.