Many industrial structures associated with railway infrastructures rely on a large number of bolted joint connections to ensure safe and reliable operation of the track and trackside furniture. Significant sums of money are spent annually to repair the damage caused by bolt failures and to maintain the integrity of bolted structures. In the UK, Network Rail (the organization responsible for rail network maintenance and safety) conducts corrective and preventive maintenance manually on 26,000 sets of points (each having approximately 30 bolted joints per set), in order to ensure operational success and safety for the travelling public. Such manual maintenance is costly, disruptive, unreliable and prone to human error. The aim of this work is to provide a means of automatically measuring the clamping force of each individual bolted joint, by means of an instrumented washer. This paper describes the development of a sensor means to be used in the washer, which satisfies the following criteria. 1. Sense changes in the clamping force of the joint and report this fact. 2. Provide compatibility with the large dynamic range of clamping force. 3. Satisfy the limitations in terms of physical size. 4. Provide the means to electronically interface with the washer. 5. Provide a means of powering the washer in situ. 6. Provide a solution at an acceptable cost. Specifically the paper focuses on requirements 1, 2 and 3 and presents the results that support further development of the proposed design and the realization of a pre-prototype system. In the paper, various options for the force sensing element (strain gage, capacitor, piezo-resistive) have been compared, using design optimization techniques. As a result of the evaluation, piezo-resistive sensors in concert with a proprietary force attenuation method, have been found to offer the best performance and cost trade-off The performance of the novel clamping force sensor has been evaluated experimentally and the results show that a smart washer can be developed to monitor the condition of bolted joints as found on railway track and points.