Measuring canopy height is important for phenotyping as it has been identified as the most relevant parameter for the fast determination of plant mass and carbon stock, as well as crop responses and their spatial variability. In this work, we develop a low-cost tool for measuring plant height proximally based on an ultrasound sensor for flexible use in static or on-the-go mode. The tool was lab-tested and field-tested on crop systems of different geometry and spacings: in a static setting on faba bean (Vicia faba L.) and in an on-the-go setting on chia (Salvia hispanica L.), alfalfa (Medicago sativa L.), and wheat (Triticum durum Desf.). Cross-correlation (CC) or a dynamic time-warping algorithm (DTW) was used to analyze and correct shifts between manual and sensor data in chia. Sensor data were able to reproduce with minor shifts in canopy profile and plant status indicators in the field when plant heights varied gradually in narrow-spaced chia (R2 = 0.98), faba bean (R2 = 0.96), and wheat (R2 = up to 0.99). Abrupt height changes resulted in systematic errors in height estimation, and short-scale variations were not well reproduced (e.g., R2 in widely spaced chia was 0.57 to 0.66 after shifting based on CC or DTW, respectively)). In alfalfa, ultrasound data were a better predictor than NDVI (Normalized Difference Vegetation Index) for Leaf Area Index and biomass (R2 from 0.81 to 0.84). Maps of ultrasound-determined height showed that clusters were useful for spatial management. The good performance of the tool both in a static setting and in the on-the-go setting provides flexibility for the determination of plant height and spatial variation of plant responses in different conditions from natural to managed systems.