The extent of single- and multi-cropping systems in any region, and potential changes to it, have consequences on food and resource use, raising important policy questions. However, addressing these questions is limited by a lack of reliable data on multi-cropping practices at a high spatial resolution, especially in areas with high crop diversity. In this paper, we describe a relatively low-cost and scalable method to identify double-cropping at the field-scale using satellite (Landsat) imagery. The process combines machine learning methods with expert labeling. We demonstrate the process by measuring double-cropping extent in a portion of Washington State in the Pacific Northwest United States--- a region with significant production of more than 60 distinct types of crops including hay, fruits, vegetables, and grains in irrigated settings. Our results indicate that the current state-of-the-art methods for identifying cropping intensity---that apply simpler rule-based thresholds on vegetation indices---do not work well in regions with a high crop diversity, and likely significantly overestimate double-cropped extent. Multiple machine learning models were able to perform better by capturing nuances that the simple rule-based approaches are unable to. In particular, our (image-based) deep learning model was able to capture nuances in this crop-diverse environment and achieve a high accuracy (96-99% overall accuracy and 83– 93% producer accuracy for the double-cropped class with standard error of less than 2.5%) while also identifying double-cropping in the right crop types and locations based on expert knowledge. Our expert labeling process worked well and has potential as a relatively low-cost, scalable approach for remote sensing applications. The product developed here is valuable to inform several policy questions related to food production and resource use.