Theoretically, the appearance of shadows in aerial imagery is not desirable for researchers because it leads to errors in object classification and bias in the calculation of indices. In contrast, shadows contain useful geometrical information about the objects blocking the light. Several studies have focused on estimation of building heights in urban areas using the length of shadows. This type of information can be used to predict the population of a region, water demand, etc., in urban areas. With the emergence of unmanned aerial vehicles (UAVs) and the availability of high- to super-high-resolution imagery, the important questions relating to shadows have received more attention. Three-dimensional imagery generated using UAV-based photogrammetric techniques can be very useful, particularly in agricultural applications such as in the development of an empirical equation between biomass or yield and the geometrical information of canopies or crops. However, evaluating the accuracy of the canopy or crop height requires labor-intensive efforts. In contrast, the geometrical relationship between the length of the shadows and the crop or canopy height can be inversely solved using the shadow length measured. In this study, object heights retrieved from UAV point clouds are validated using the geometrical shadow information retrieved from three sets of high-resolution imagery captured by Utah State University’s AggieAir UAV system. These flights were conducted in 2014 and 2015 over a commercial vineyard located in California for the USDA Agricultural Research Service Grape Remote sensing Atmospheric Profile and Evapotranspiration Experiment (GRAPEX) Program. The results showed that, although this approach could be computationally expensive, it is faster than fieldwork and does not require an expensive and accurate instrument such as a real-time kinematic (RTK) GPS.