Wind is a naturally variable resource that fluctuates across timescales and, by the same token, the electricity generated by wind also fluctuates across timescales. At longer timescales, i.e., hours to days, synoptic-scale weather systems, notably cold fronts during South African winter months, are important instigators of strong wind conditions and variability in the wind resource. The variability of wind power production from aggregates of geographically disperse turbines for the passage of individual cold fronts over South Africa was simulated in this study. When considering wind power variability caused by synoptic-scale weather patterns, specifically cold fronts, the timescale at which analysis is conducted was found to be of great importance, as relatively small mean absolute power ramps at a ten-minute temporal resolution, order of 2-4% of simulated capacity, can result in large variations of total wind power production (at the order of 32–93% of simulated capacity) over a period of three to four days as a cold front passes. It was found that when the aggregate consists of a larger and more geographically dispersed set of turbines, as opposed to a smaller set of turbines specifically located within cold-front dominated high wind areas, variability and the mean absolute ramp rates decrease (or gets ‘smoothed’) across the timescales considered. It was finally shown that the majority of large simulated wind power ramp events observed during the winter months, especially at longer timescales, are caused by the passage of cold fronts.