The Confederation Bridge spans across the Northumberland Strait in Eastern Canada connecting Prince Edward Island to mainland Canada through New Brunswick. Due to the presence of ice during each winter, the bridge piers are subjected to ice loads. A comprehensive permanent monitoring program has been implemented to observe and measure the ice–structure interaction events at two piers since the start of the bridge operations in 1998. This study uses the derived ice loads on one pier, and the associated event attributes for 100 selected events. Flexural failure models are used to determine theoretical loads of the selected interaction events. It is found that the weight of the total ice rubble pile and the physical and mechanical properties of the ice sheet are the dominant parameters affecting the ice load exerted on the conical structure. A semi-empirical correlation is developed to relate the ice load with those parameters for the Confederation Bridge.