Soil moisture is a critical element in the hydrological cycle especially in a semiarid or arid region. Point measurement to comprehend the soil moisture distribution contiguously in a vast watershed is difficult because the soil moisture patterns might greatly vary temporally and spatially. Space-borne radar imaging satellites have been popular because they have the capability to exhibit all weather observations. Yet the estimation methods of soil moisture based on the active or passive satellite imageries remain uncertain. This study aims at presenting a systematic soil moisture estimation method for the Choke Canyon Reservoir Watershed (CCRW), a semiarid watershed with an area of over 14,200 km2 in south Texas. With the aid of five corner reflectors, the RADARSAT-1 Synthetic Aperture Radar (SAR) imageries of the study area acquired in April and September 2004 were processed by both radiometric and geometric calibrations at first. New soil moisture estimation models derived by genetic programming (GP) technique were then developed and applied to support the soil moisture distribution analysis. The GP-based nonlinear function derived in the evolutionary process uniquely links a series of crucial topographic and geographic features. Included in this process are slope, aspect, vegetation cover, and soil permeability to compliment the well-calibrated SAR data. Research indicates that the novel application of GP proved useful for generating a highly nonlinear structure in regression regime, which exhibits very strong correlations statistically between the model estimates and the ground truth measurements (volumetric water content) on the basis of the unseen data sets. In an effort to produce the soil moisture distributions over seasons, it eventually leads to characterizing local- to regional-scale soil moisture variability and performing the possible estimation of water storages of the terrestrial hydrosphere.