A method is presented to estimate the cost of sustaining a set of bridge connections. The term “sustaining a bridge connection” means the rehabilitation, replacement, or both of an existing bridge to sustain the ability of users (drivers, pedestrians, etc.) to cross the given obstacle (river, creek, other roadway, etc.). The method was developed to estimate the cost of sustaining the bridge connections in Hampton Roads (southeastern Virginia) through the year 2040. After existing software was found to be a mismatch for the task, a simple, robust, spreadsheet method was developed to estimate costs—according to bridge age—on the basis of actual recent costs by bridge age. This method can be calibrated with local bridge cost and inventory data to apply it to estimating the cost of sustaining any set of bridge connections.