A study of the climatic characteristics and annual runoff of the Volga and Severnaya Dvina rivers demonstrates that, on the East European Plain (EEP), Early Twentieth Century Warming (ETCW) manifested in a multiyear drought between 1934 and 1940; this drought has no analogues in this region in terms of intensity and duration according to Palmer’s classification, and caused extreme hydrological events. The circulation conditions during this event were characterized by an extensive anticyclone over Eastern Europe, combined with a cyclonic anomaly in the circumpolar region. An analysis of the spatial features of sea surface temperature (SST) anomalies indicate that the surface air temperature (SAT) anomalies in July on the EEP during ETCW were related not only to the North Atlantic (NA) warming and positive AMO phase, but also to a certain spatial pattern of SST anomalies characteristic of the 1920–1950 period. The difference between the SST anomalies of the opposite sign in the different NA zones, used as the indicator of the obtained spatial pattern, shows the quite close relations between the July SAT anomalies on the EEP and the atmospheric circulation patterns responsible for them. The positive phase of the Atlantic Multidecadal Oscillation (AMO) and the expansion of the subtropical high-pressure belt to the north and to the east can be considered as global-scale drivers of this phenomenon. The AMO also impacts the sea ice cover in the Barents–Kara Sea region, which, in turn, could have led to specific atmospheric circulation patterns and contributed to droughts on the EEP in the 1930s.