Turfgrass in equine sports has clear advantages over other types of reinforcement but adds complexity to the management. This study investigates factors that influence the turfgrass’ surface performance and how the use of a drainage package and a geotextile reinforcement affect quantitative measurements of turfgrass. The measurements are made using affordable, lightweight testing tools that are readily available or easily constructed. Eight boxes with turfgrass over a mix of the arena with peat at a consistent depth were tested for volumetric moisture content (VMC %) with time–domain reflectometry (TDR), the rotational peak shear device (RPS), the impact test device (ITD), soil cone penetrometer (SCP), and the Going Stick (GS). Results obtained using TDR, RPS, ITD, SCP, and GS indicate that the presence of the geotextile and drainage package was mainly detected by VMC (%), SCP detected geotextile addition, and GS detected the interaction of geotextile × drainage package. Linear regression showed SCP and GS are related to geotextile and was positively correlated between them and negatively with VMC (%). The testing showed some limitations of these devices, mainly related to moisture content and sod composition, but the potential exists to utilize these devices for quality control as well as for the monitoring of maintenance of the surfaces when controlling the range of both VMC (%) and sod constitution.