Many US states have targets for vastly expanding electricity generation from renewable resources. As installed wind capacity increases, several factors can lead to the curtailment of potential wind-generated electricity. Reliably estimating wind power outputs remains a challenge given the dearth of available hub height-altitude wind speed data and measured outputs from newer turbines. A methodology to make such estimates with large increases in wind capacity is described. A regional wind power model, including subroutines for evaluating Statewide grid constraints, and a linear program to solve the model were developed to assess capacity factors and curtailments with deep penetration of wind power into an existing grid under several constrained scenarios implied by demand, baseload generation and transmission. Actual zonal demand and interzonal transmission limits were used for the New York State electricity grid, which has significant potential for wind power mostly distant from the concentrated electricity demand in and around New York City. 0.015% of the total number of 5-minute demand values over the 6-year analysis period. As such, any assumptions required to complete the zonal time series are not expected to have a significant impact on the results of the analysis.