What path does Jacob take to uncover his Grandfather's last words? What progress does he make?

Grandpa Portman's dying words are cryptic instructions that will eventually lead Jacob to Cairnholm and all the secrets it holds. Up until this point, he has kept Jacob's peculiar identity from him in order to protect him, and allowed him to believe that all the stories he used to tell were fake. Now, though, in his dying moments, he chooses to set his grandson on the path to the truth.

Find the bird. In the loop. On the other side of the old man's grave. September third, 1940.