Similar story. The old Apple Maps icon was where the N De Anza Boulevard crossed over the Junipero Serra Freeway. Center of the old icon [0] was One Infinite Loop, top left of the icon was the Cupertino Hotel.

Going from the Cupertino Hotel to One Infinite Loop on foot felt like I was risking life and limb, despite it having pedestrian lights [1].

[0] http://thetrendler.com/wp-content/uploads/2015/10/Maps-Icons...

[1] https://goo.gl/maps/ZMBq8RzpZLc6xwM97