The aim of this study is to assess the winter wheat planting (WWP) area in Henan Province and investigate its temporal and spatial variations by using remote sensing (RS) technology. A spectral angle mapper (SAM) was adopted to identify the WWP area of each district divided by the hierarchical grades of land surface drought index during 2001-2015. The results obtained show the expediency of monitoring the WWP areas at the regional scale via drought regionalization, which provides a goodness-of-fit R2 =0.933, a mean relative error MRE=49,118 ha, and an overall accuracy up to 90.24%. The major WWP areas in Henan Province were located in Zhoukou, Zhumadian, Shangqiu, Nanyang, and Xinxiang prefecture-level cities. Two representative sites are mountainous districts, with rich water resources or high urbanization rate, which have a low probability of WWP. Both sites exhibited a strongly manifested evolution of WWP areas, which could be attributed to extremely cold weather conditions, crop alternation, the popularization of new varieties, and fast expansion of built-up areas. The results of this study are instrumental in the analysis of crop planting variation characteristics, which should be taken into account in the further decision-making process related to the crop planting strategies.