This paper is concerned with the estimation of radio communication distance when both the transmitter and receiver are arbitrarily distributed on a random rough surface such as desert, terrain, sea surface and so on. First, we simulate electromagnetic wave propagation along the rough surface by using the discrete ray tracing method (DRTM) proposed by authors recently. Second, we determine three parameters by conjugate gradient method (CGM) combined with the method of least-squares. Finally, we derive an analytical expression which can estimate the maximum communication distance when the input power of a transmitter and the minimum detectable electric intensity of a receiver are specified. Random rough surfaces are assumed to be Gaussian, pn-th order power law or exponential distributions.