The role of the Valdai Hills and the Valdai Lake area in ensuring the fullness of the sources of the Volga River and its current trends against the background of climate change is presented. It is shown that the “water-making functions” of the upland landscape are initially determined by two general properties of the relief: its invariance as a “framework of life” and its changeable evolution under the influence of endogenous and exogenous factors. The “Cradle of the Volga” in relation to the Valdai Hills and specifically the Baltic-Caspian watershed is a set of conditions that allow the formation of runoff in the upper reaches of the river. Among the main ones that determine the conservation of runoff in the average annual volume are the state of rivers, lakes, and swamps, the minimization of anthropogenic impacts (regulation of runoff, plowing, catchment, deforestation, development and pollution of the coastline, etc.), and, in general, nature protected areas (creation of them at the source of the river). Based on the materials from the monitoring of the climate and hydrological regime of the region carried out by the Valdai branch of the State Hydrological Institute (Valdai), the main trends of the Volga River runoff factors in the upper reaches have been identified. The share of water-regulating, water-saving, and assimilation functions in the total volume of ecosystem services in the landscapes of the Valdai Hills is shown. It is concluded that the modern growth of recreational impact on the catchments of the sources of the Volga River can reduce the positive effect of the functioning of nature protected areas on them. The priority issues in preserving the “cradle of the Volga” should be the regulation of recreational loads on the landscapes of the Valdai Hills, rehabilitation of disturbed forest ecosystems, and monitoring of the volume and quality of runoff.