Effectively evaluating the effectiveness of bridge strengthening is a necessary means to ensure the normal operation of existing strengthened bridges, especially when evaluating the effectiveness of bridge strengthening without interrupting normal traffic. Based on a distributed long-gauge Fiber Bragg Grating (FBG) sensor, this paper derived the macro-strain influence line (MSIL) formula for a simply supported beam bridge under a moving vehicle load, studied the changes in the MSIL at the bottom of the beam under the vehicle load before and after the prestressed CFRP plate strengthening, and proposed a rapid evaluation method for the strengthening effect based on the amplitude of the MSIL as the evaluation index for the strengthening effect. Finally, the prestressed CFRP-strengthened steel beam was tested under the moving vehicle load. The theoretical analysis and the experimental results confirm that under the load of moving vehicles, the macro-strain–time history amplitude of the strengthened steel beams under different prestressed tensioning conditions is different. The amplitude of the macro-strain time history of the strengthened bridge is reduced compared to before strengthening, and the local strengthening effect of the bridge can be monitored by the amplitude change in a single sensor. The change in global stiffness can be evaluated by monitoring the MSIL obtained from multiple long-gauge strain sensors.