We investigated the predictive capability of various configurations of the Weather Research and Forecasting (WRF) model version 4.4, to predict hub height offshore wind speed and wind power density in the Northeast US wind farm lease areas. The selected atmospheric conditions were high-pressure systems (anticyclones) coinciding with wind speed below the cut-in wind turbine threshold. There are many factors affecting the potential of offshore wind power generation, one of them being low winds, namely wind droughts, that have been present in future climate change scenarios. The efficiency of high-resolution hub height wind prediction for such events has not been extensively investigated, even though the anticipation of such events will be important in our increased reliance on wind and solar power resources in the near future. We used offshore wind observations from the Woods Hole Oceanographic Institution’s (WHOI) Air–Sea Interaction Tower (ASIT) located south of Martha’s Vineyard to assess the impact of the initial and boundary conditions, number of model vertical levels, and inclusion of high-resolution sea surface temperature (SST) fields. Our focus has been on the influence of the initial and boundary conditions (ICBCs), SST, and model vertical layers. Our findings showed that the ICBCs exhibited the strongest influence on hub height wind predictions above all other factors. The NAM/WRF and HRRR/WRF were able to capture the decreased wind speed, and there was no single configuration that systematically produced better results. However, when using the predicted wind speed to estimate the wind power density, the HRRR/WRF had statistically improved results, with lower errors than the NAM/WRF. Our work underscored that for predicting offshore wind resources, it is important to evaluate not only the WRF predictive wind speed, but also the connection of wind speed to wind power.