Identifying agricultural fields that grow cabbage in the highlands of South Korea is critical for accurate crop yield estimation. Only grown for a limited time during the summer, highland cabbage accounts for a significant proportion of South Korea’s annual cabbage production. Thus, it has a profound effect on the formation of cabbage prices. Traditionally, labor-extensive and time-consuming field surveys are manually carried out to derive agricultural field maps of the highlands. Recently, high-resolution overhead images of the highlands have become readily available with the rapid development of unmanned aerial vehicles (UAV) and remote sensing technology. In addition, deep learning-based semantic segmentation models have quickly advanced by recent improvements in algorithms and computational resources. In this study, we propose a semantic segmentation framework based on state-of-the-art deep learning techniques to automate the process of identifying cabbage cultivation fields. We operated UAVs and collected 2010 multispectral images under different spatiotemporal conditions to measure how well semantic segmentation models generalize. Next, we manually labeled these images at a pixel-level to obtain ground truth labels for training. Our results demonstrate that our framework performs well in detecting cabbage fields not only in areas included in the training data but also in unseen areas not included in the training data. Moreover, we analyzed the effects of infrared wavelengths on the performance of identifying cabbage fields. Based on the results of our framework, we expect agricultural officials to reduce time and manpower when identifying information about highlands cabbage fields by replacing field surveys.