A unique map generation system and method are provide that facilitates automatically detecting a user's (or user's device's) current location and generating at least one customized map view of a static location based on the current (dynamic) location of the user. Many portable and handheld devices have very small user interfaces and limited means of entering alphanumeric information. Network-based content such as web pages offer generic map views of a location of the content but without consideration of the user's location. Traditional systems require entry of the relevant data (e.g., address information) in order to obtain or generate a map view or directions. However, in the subject system, the user's location can be automatically detected and “entered” and a customized map view for this current location in relation to the content's location can be created—thus with minimal user input or action.