Systems and methods to generate visual overlays on a graphical user interface (GUI) based calendar which is viewable according to numerous views, such as a month view, year view, decade view, etc. The calendar may be associated with a library (“media library”) of various objects (e.g., images, videos, music, documents) stored across one or more storage devices. The system may generate a date-range overlay in which the user creates a query, or may generate an autonomously extracted overlay from a container of media objects. The system autonomously extracts date(s) from media files in the container or query result and generates an overlay on the calendar which corresponds to the autonomously extracted date(s) of the files in the container or query. The generated overlay may be displayed on the calendar as a single date-range overlay or as individual overlays associated with each media object in the container or query.