Friction occurs in the processes of transport and storage of granular plant materials used in the energy (RES—Renewable Energy Sources) and food sectors. This paper presents the results of a study on the impact of the moisture content of the material and the number of its contact points with a smooth surface (a steel sheet) on the process of friction in grains of wheat and buckwheat. The friction process was studied for four different levels of moisture (9.5%, 13.5%, 17.5% and 21.5%) and three different average numbers of contact points. To measure the force of friction, an universal testing machine with appropriate instrumentation was used. To determine the number of contact points, computer imaging analysis was conducted. An increase in static and kinetic friction was observed along with the increase in moisture level and the increase in the number of contact points. Correlation and regression analysis was performed for the data obtained.