In this paper, a relatively less studied class of structures is presented based on the research conducted on Florida's movable bridges over the last several years. Movable bridges consist of complex structural, mechanical and electrical systems that provide versatility to these bridges, but at the same time, create intermittent operational and maintenance challenges. Movable bridges have been designed and constructed for some time; however, there are fewer studies in the literature on movable bridges as compared to other bridge types. In addition, none of these studies provide a comprehensive documentation of issues related to the condition of movable bridge populations in conjunction with possible monitoring applications specific to these bridges. This paper characterises and documents these issues related to movable bridges considering both the mechanical and structural components. Considerations for designing a monitoring system for movable bridges are also presented based on inspection reports and expert opinions. The design and implementation of a monitoring system for a representative bascule bridge are presented along with long-term monitoring data. Various movable bridge characteristics such as opening/closing torque, bridge balance and friction are shown since these are critical for maintenance applications on mechanical components. Finally, the impact of environmental effects (such as wind and temperature) on bridge mechanical characteristics is demonstrated by analysing monitoring data for more than 1000 opening/closing events.