Hydrochemical and geophysical methods were used to assess saline paleo-water mass transfer induced by piston flow in the alluvial aquifer of the Oltrepò Pavese plain (northern Italy). The surface aquifer shows salinity contamination from a Tertiary substrate of marine origin, due to mixing of the shallower fresh groundwater with the Po Plain’s deep brines. The study also used continuous monitoring of groundwater electrical conductivity, temperature and piezometric levels. Well logging and geophysical imaging, conducted at different times, revealed that the contamination varies over time, and that the water salinity and the depth of the transition zone (between the surface freshwaters and the deep saline waters) are subject to modifications. This is due to a pressure transfer—and, subsequently, mass transfer−from the groundwater circuits of the nearby Apennine mountains. It suggests that a hydraulic connection exists between the fractured Apennine water circuits and the deeper Mio-Pliocene and Tertiary saline-water circuits found below the plain’s alluvial aquifer. Coinciding with significant recharge episodes that affect Apennine water circuits (prolonged rainfall and snow melt at mid-high altitudes), there is a pressure transfer transmitted along the water circuits in which saline water resides, providing an impulse to rise along the discontinuities and reach the alluvial aquifer. The conceptual model is supported by evidence that wells constructed in correspondence to hydraulically active tectonic discontinuities are affected by the arrival of saline waters with variable delays, while wells sited in sectors not affected by tectonic discontinuities are diluted by ‘fresh’ waters connected to alluvial aquifer recharge.