The expansion of offshore wind power as part of a transition to low-carbon electricity generation presents challenges for the resilience of power grids. One strategy to address this challenge is to rely on imports from neighboring power systems with excess production capacity. However, constraints due to grid topography and internal generation may limit the import capacity. This study uses a quasi-dynamic power flow simulation based on the IEEE 39-bus system to assess the limits of increasing offshore wind power penetration on the grid’s ability to meet demand. The model is a synthetic grid based on the topography of the New England power grid, loads are held constant, and between one and five conventional generators are replaced with wind farms while the remaining generators are constrained by ramp rates. To model wind power production, we have constructed a composite wind farm power curve by smoothing the power curve of a single wind turbine generator. Wind speed data are retrieved from single locations in the WIND Toolkit Long-Term Ensemble Dataset with five-minute resolution. We find that high levels of wind power penetration increase the risk of unmet demand due to physical and operational power flow constraints in certain wind conditions. We also identify critical network elements and imported power limits. These findings both expand and challenge the findings of previous work by shedding light on underlying constraints while considering future wind power technology.