A portable entertainment system for use with a vehicle, such as a bicycle, that amplifies a signal from a portable media device docked therein, and includes a substantially cylindrical housing unit having a speaker and a portable media device docking unit, the speaker being communicably coupled with the docking unit and outputting the amplified signal, a remote control unit controlling a level of the amplified signal output by the speaker and controlling functions of the portable media device docked in the docking unit, and an impact resistant suspension mounting bracket stably securing the housing unit to a frame of the vehicle.