An endoscope insertion shape observation apparatus includes a processor, and the processor: detects a travelling direction of a first position detection member and a travelling direction of a second position detection member out of plural position detection members provided in an insertion portion inserted into a lumen of a subject, the first position detection member being provided on a distal end side of a bending portion of the insertion portion, the second position detection member being provided on a proximal end side of the bending portion; detects a stretch start timing in which the lumen starts stretching, based on detection results of the travelling directions and finds position coordinates of a predetermined position of the bending portion in the detected stretch start timing as a manual compression point; and causes a compression position display that indicates the position found as the manual compression point to be presented on a monitor.