The thermal response of a large and complex city including the energy production aspects of it are explored using urbanized atmospheric mesoscale modeling. The Weather Research and Forecasting (WRF) Mesocale model is coupled to a multilayer urban canopy model that considers thermal and mechanical effects of the urban environment including a building scale energy model to account for anthropogenic heat contributions due to indoor–outdoor temperature differences. This new urban parameterization is used to evaluate the evolution and the resulting urban heat island (UHI) formation associated to a 3-day heat wave in New York City (NYC) during the summer of 2010. High-resolution (250 m) urban canopy parameters (UCPs) from the National Urban Database were employed to initialize the multilayer urban parameterization. The precision of the numerical simulations is evaluated using a range of observations. Data from a dense network of surface weather stations, wind profilers, and Lidar measurements are compared to model outputs over Manhattan and its surroundings during the 3-days event. The thermal and drag effects of buildings represented in the multilayer urban canopy model improves simulations over urban regions giving better estimates of the 2 m surface air temperature and 10 m wind speed. An accurate representation of the nocturnal urban heat island registered over NYC in the event was obtained from the improved model. The accuracy of the simulation is further assessed against more simplified urban parameterizations models with positive results with new approach. Results are further used to quantify the energy consumption of the buildings during the heat wave, and to explore alternatives to mitigate the intensity of the UHI during the extreme event.