Satellite remote sensing is well demonstrated to be a powerful tool for investigating ancient land use in Southwest Asia. However, few regional studies have systematically integrated satellite-based observations with more intensive remote sensing technologies, such as drone-deployed multispectral sensors and ground-based geophysics, to explore off-site areas. Here, we integrate remote sensing data from a variety of sources and scales including historic aerial photographs, modern satellite imagery, drone-deployed sensors, and ground-based geophysics to explore pre-modern land use along the Upper Diyala/Sirwan River in the Kurdistan Region of Iraq. Our analysis reveals an incredible diversity of land use features, including canals, qanats, trackways, and field systems, most of which likely date to the first millennium CE, and demonstrate the potential of more intensive remote sensing methods to resolve land use features. Our results align with broader trends across ancient Southwest Asia that document the most intensive land use in the first millennium BCE through the first millennium CE. Land use features dating to the earlier Bronze Age (fourth through second millennium BCE) remain elusive and will likely require other investigative approaches.