A number of satellite missions have the capability to provide surface soil moisture information at a range of spatial and temporal scales. However, the validation of such products heavily relies on point measurements from permanent stations, which may or may not be representative of the larger scale soil moisture conditions. Hence, methods need to be developed that allow the sampling of surface soil moisture on the ground across large scales over a reasonably short time scale, in order to capture the spatial variability within a footprint, or to provide spatially sufficiently large data sets to validate high-resolution products, be they at their native resolution or downscaled. In this study, two field-scale ground sampling techniques, namely stationary and roving Cosmic Ray Probes, are compared against a high-resolution satellite product. The data are compared for their temporal performance as well as with a focus on capturing the correct spatial variability. The challenge is the inherently different sensing depth of the various technologies. It is shown that this may largely be overcome through scaling the products.