A monitoring system for determining a stickup height of a drill string. The monitoring system includes a video camera operable to facilitate a digital image, a block position sensor operable to facilitate block position measurements, and/or a processing device. The processing device receives the digital image, recognizes an upper end of the drill string or a connection joint of the drill string on the digital image, and determines the stickup height based on location of the upper end of the drill string or the connection joint of the drill string on the digital image. The processing device may also or instead record a pipe tally indicative of a length of each drill pipe and a location of each drill pipe within the drill string, receive the block position measurements, and determine the stickup height based on the pipe tally and block position measurements.