Mechanically induced nonlinearities in nano-electromechanical systems (NEMSs) are typically avoided in design due to their unpredictable nature; however, by incorporating these normally unwanted nonlinear and chaotic phenomena, the performance of NEMS devices displays substantially different characteristics opening a broad new range of potential applications for their use. In this work, experiments have been conducted for probing the chaotic boundary of a circular membrane mechanical resonator with and without a silicone nanowire array (Si NWA). The NWA resonator can transition from linear to nonlinear quasi-periodic behaviour, and further transition into a chaotic state at resonance. Moreover, the NWA resonator demonstrated a high level of complex nonlinear behaviours, as the device expands the power spectral response from a single frequency at a linear regime to a wideband continuous frequency spectrum when chaotic behaviour was initiated; the threshold power of this transition decreased with a smaller NWA diameter. It was also observed that the NWA resonator had higher damping compared to the resonator without a NWA; however, as the vibration velocity of the NWA resonator increased, complex air damping and thin squeeze film damping lowered the threshold for probing the chaotic boundary condition of the NWA resonator.