This paper is an attempt to investigate the rock indentation behaviors of a conical pick under different loading rates (1, 2, 3, and 4 mm/min), indenter types (sharp and blunt indenters), and types of rock (concrete, limestone, granite). Serial indentation tests by indenters were first performed by an automatic universal testing machine and monitored by an i-SPEED high-speed camera to record the peak pick force, indentation depth, rock fracture area, and rock failure process. Accordingly, the effect of loading rates, rock brittleness, and pick type on rock indentation behaviors was subsequently analyzed for a sound understanding of rock fragmentation mechanisms with indenters. It was found that higher loading rates necessitate a higher pick force and indentation depth to achieve rock fragmentation, resulting in a larger fractured area. Notably, a positive linear relationship exists between loading rates, rock-breaking forces, and fracture areas. A sharp indenter induces multiple cycles of repeated crushing and chipping phases, resulting in an arcuate-shaped fracture pattern with a smaller fractured area. Conversely, the rounded blunt indenter leads to a single stage of compression, with cracks propagating directly through the rock specimen, producing a larger fractured area. In addition, rock brittleness is another key factor to control rock failure efficiency, with tensile strength serving as a significant component.