As the most severe drought over the Northeastern United States (NEUS) in the past century, the 1960s drought had pronounced socioeconomic and natural impacts. Although it was followed by a persisting wet period, the conditions leading to the 1960s extreme drought could return in the future, along with its challenges to water management. To project the characteristics and potential consequences of such a future drought, pseudo-global warming simulations using the Weather Research and Forecasting Model are performed to simulate the dynamical conditions of the historical 1960s drought, but with modified thermodynamic conditions under the RCP8.5 scenario in the early (2021-2027), middle (2041-2047) and late (2091-2097) 21st century. Our analysis focuses on essential hydroclimatic variables including temperature, precipitation, evapotranspiration, soil moisture, snowpack and surface runoff. In contrast to the historical 1960s drought, similar dynamical conditions will generally produce more precipitation, increased soil moisture and evapotranspiration, and reduced snowpack. However, we also find that although wet months get much wetter, dry months may become drier, meaning that wetting trends are most significant in wet months but are essentially negligible for extremely dry months with negative monthly mean net precipitation. For these months, the trend towards wetting conditions provides little relief from the effects of extreme dry months. These conditions may even aggravate water shortages due to an increasingly rapid transition from wet to dry conditions. Other challenges emerge for residents and stakeholders in this region, including more extreme hot days, record-low snow pack, frozen ground degradation and subsequent decreases in surface runoff.