A software and/or hardware facility for generating menu trails for a portable media player. A menu trail is a visual cue to a user, repeated on each menu item in the media player navigation interface, that highlights a path for the user to follow to a content item stored on or accessible by the media player, or to a capability of the media player. Menu trails may highlight new content and capabilities, or may highlight existing content or capabilities. A user using the media player may easily follow the visual cues through the player's menus in order to navigate to the content item or capability.