Understanding the hydrological and hydrogeochemical responses of hillslopes and other small scale groundwater systems requires mapping the velocity and direction of groundwater flow relative to the controlling subsurface material features. Since point observations of subsurface materials and groundwater head are often the basis for modelling these complex, dynamic, three-dimensional systems, considerable uncertainties are inevitable, but are rarely assessed. This study explored whether piezometric head data measured at high spatial and temporal resolution over six years at a hillslope research site provided sufficient information to determine the flow paths that transfer nitrate leached from the soil zone through the shallow saturated zone into a nearby wetland and stream. Transient groundwater flow paths were modelled using MODFLOW and MODPATH, with spatial patterns of hydraulic conductivity in the three material layers at the site being estimated by regularised pilot point calibration using PEST, constrained by slug test estimates of saturated hydraulic conductivity at several locations. Subsequent Null Space Monte Carlo uncertainty analysis showed that this data was not sufficient to definitively determine the spatial pattern of hydraulic conductivity at the site, although modelled water table dynamics matched the measured heads with acceptable accuracy in space and time. Particle tracking analysis predicted that the saturated flow direction was similar throughout the year as the water table rose and fell, but was not aligned with either the ground surface or subsurface material contours; indeed the subsurface material layers, having relatively similar hydraulic properties, appeared to have little effect on saturated water flow at the site. Flow path uncertainty analysis showed that, while accurate flow path direction or velocity could not be determined on the basis of the available head and slug test data alone, the origin of well water samples relative to the material layers and site contour could still be broadly deduced. This study highlights both the challenge of collecting suitably informative field data with which to characterise subsurface hydrology, and the power of modern calibration and uncertainty modelling techniques to assess flow path uncertainty in hillslopes and other small scale systems.