A system and method of providing advertisements to vehicles is disclosed. An apparatus that incorporates teachings of the present disclosure may include, for example, a system having at least one wireless communication access point deployed along a freeway, a database for storing one or more media files associated with one or more advertisements, the database storing information concerning the types of media files supported by a number of media systems of a corresponding number of user vehicles, and a server coupled to the database having access to the at least one wireless communication access point. The server can direct the wireless communication access point to transmit one or more advertisements to the portable communication devices according to one or more types of media files determined to be supported by the media systems, and the corresponding user vehicles being proximately located to a freeway exit. Additional embodiments are disclosed.