A system and method for generating a content based, custom labeled map is provided. A request for a map is received. The request includes a geographical area to be displayed in the map and a type of content item to be displayed in the map. A plurality of orientation points to display on the map is determined based on a ranking of locations in the geographical area, and one or more pieces of content to be associated with each orientation point is determined. Each orientation point is ranked based in part on ranks of the one or more pieces of content associated with each orientation point. A map is generated to display at the locations of the plurality of orientation points the pieces of content associated with each orientation point at a level of prominence that is based on the ranking of each orientation point.