The accuracy of dryland crop classification using satellite-based synthetic aperture radar (SAR) data is often unsatisfactory owing to the similar dielectric properties that exist between the crops and their surroundings. The main objective of this study was to improve the accuracy of dryland crop (maize and cotton) classification by combining multitype features and multitemporal polarimetric SAR (PolSAR) images in Hebei plain, China. Three quad-polarimetric RADARSAT-2 scenes were acquired between July and September 2018, from which 117 features were extracted using the Cloude–Pottier, Freeman–Durden, Yamaguchi, and multiple-component polarization decomposition methods, together with two polarization matrices (i.e., the coherency matrix and the covariance matrix). Random forest (RF) and support vector machine (SVM) algorithms were used for classification of dryland crops and other land-cover types in this study. The accuracy of dryland crop classification using various single features and their combinations was compared for different imagery acquisition dates, and the performance of the two algorithms was evaluated quantitatively. The importance of all investigated features was assessed using the RF algorithm to optimize the features used and the imagery acquisition date for dryland crop classification. Results showed that the accuracy of dryland crop classification increases with evolution of the phenological period. In comparison with SVM, the RF algorithm showed better performance for dryland crop classification when using full polarimetric RADARSAT-2 data. Dryland crop classification accuracy was not improved substantially when using only backscattering intensity features or polarization decomposition parameters extracted from a single-date image. Satisfactory classification accuracy was achieved using 11 optimized features (derived from the Cloude–Pottier decomposition and the coherency matrix) from 2 RADARSAT-2 images (acquisition dates corresponding to the middle and late stages of dryland crop growth). This study provides an important reference for timely and accurate classification of dryland crop in Hebei plain, China.