A distributed online fiber sensing system based on the phase-sensitive optical time domain reflectometer (Φ-OTDR) enhanced by the drawing tower fiber Bragg grating (FBG) array is presented and investigated experimentally for monitoring the galloping of overhead transmission lines. The chirped FBG array enhanced Φ-OTDR sensing system can be used to measure the galloping behavior of the overhead transmission lines (optical phase conductor or optical power ground wire), which are helpful for monitoring the frequency response characteristics of the ice-induced galloping, evaluating the motion tendencies of these cables, and avoiding the risk of flashover during galloping. The feasibility of the proposed online monitoring system is demonstrated through a series of experiments at the Special Optical Fiber Cable Laboratory of State Grid Corporation of China (Beijing, China). Results show that the proposed system is effective and reliable for the monitoring of galloping shape and characteristic frequency, which can predict the trend of destructive vibration behavior and avoid the occurrence of cable breaking and tower toppling accidents, and these features are essential for the safety operation in smart grids.