A portable entertainment system for use with a vehicle, such as a bicycle or motorcycle, and a helmet. The system may include a vehicle subsystem and a helmet subsystem. The vehicle subsystem includes a mounting device having at least one port, the mounting device adapted to connect to the bicycle, and a portable computing device positionable in the at least one port, the portable computing device having one or more digitized audio files thereon. A wireless transmitter is coupled with the portable computing device, the wireless transmitter transmitting a digitized audio signal when the portable computing device is playing a digitized audio file. The helmet subsystem includes a wireless receiver positioned on the helmet, the wireless receiver receiving the digitized audio signal from the wireless transmitter; a processor coupled with the wireless receiver, the processor converting the digitized audio signal to an analog audio signal; and speaker ear cones positioned on the helmet, the speaker ear cones connected with the processor for creating an audible audio signal from the analog audio signal. The speaker ear cones are positioned on the helmet near the user's ears without the speaker ear cones contacting the user's ears. In this manner, the user can hear traffic sounds, as needed for safety reasons, and the user can operate the vehicle without having wires interfering with the operation of the vehicle.