The old Post Road of Colonial times traveled up the East Side from the foot of Manhattan before cutting west, entering what is now Central Park at 92nd Street, where it became, more or less, the current route of East Drive and McGowan’s Pass, before heading on up north.
Here we see it in 1861, just north of 42nd Street. By this point the Post Road had long been subsumed into Second Avenue.
This drawing is very funny in itself—the girl with the hoop; the stately family and couples strolling down the moonscape; the big house now “beached” onto a high, rocky island after repeated gradings of the unpaved road. The artist, Napoleon Sarony, was a veteran comic illustrator who would shortly move into photography, in which career he would make many timeless portraits of celebrated persons, such as Oscar Wilde and General Sherman.
The dips in the avenue are still there, though ever-more-flattened, as this accompanying screen-grab from Googlemaps shows. We look almost in vain for some surviving building, and then we see it: this one tenement (red arrow) at the corner of 44th and Second, still fresh and lonely in 1861.