As worldwide landslides frequently result in enormous casualties and huge economic losses, new landslide monitoring technologies are urgently required to develop for preventing and mitigating landslide hazard. In this paper, a self‐powered, flexible, timbo‐like triboelectric force and bend sensor (TTEFBS) is proposed and implemented, with the aim of effectively monitoring landslides. The fabricated TTEFBS, based on a single‐electrode working mode, consists of a timbo‐like inner polydimethylsiloxane (PDMS) core coated with a carbon electrode and an outer silicon rubber tube. Owing to the novel structure and sensing mechanism, the TTEFBS achieves high sensitivities (5.20 V N−1 under pressing and 1.61 V rad−1 under bending), fast response/relaxation time (<6 ms), and long‐term stability/reliability (more than 40 000 cycles). Furthermore, a wireless and distributed monitoring system using an array of TTEFBSs is developed for systematically detecting rockfalls, deep‐seated landslides, and superficial landslides. Additionally, a zigzag‐structured triboelectric nanogenerator (Z‐TENG), characterized by an open‐circuit voltage of ≈2058 V and a short‐circuit current of ≈154 µA, is successfully fabricated for scavenging energy from moving cars to provide power in wild environments, thereby forming a self‐powered monitoring system. This work may further inspire rapid progress of TENG in applications of wireless, distributed sensing, and environmental/infrastructure monitoring.