A methodology is proposed for estimating the shielding failure flashover rate (SFFOR) of single-circuit overhead lines with horizontal phase configuration. An application to a 66 kV overhead line is presented. A stochastic lightning attachment model is employed, based on the concept of fractal structures, to compute the probability of shielding failure to the line. Results of stochastic modeling are combined with those of an ATP-EMTP model for estimating the critical lightning currents causing flashover of the line insulation. Shielding failure results of the proposed methodology are compared and discussed with results obtained employing the methodology of the IEEE Std 1243. Innovation of this work lies in estimating the SFFOR of overhead lines by considering the stochastic nature of lightning attachment, physical criteria associated with leader discharges’ inception and propagation, as well as electromagnetic transient simulations to predict lightning-related flashover to overhead lines accurately.