Circumferential milling is used in wood processing, yet it generates vast quantities of dust and chips in a single pass, highlighting the need to predict chip dispersion and prevent associated hazards. This article presents findings from a theoretical and experimental analysis of chip size and kinematics of pine wood during cutting. A chip diffusion boundary surface model was established and its key parameters were determined through CCD testing. Results reveal that chip diffusion can be divided into three distinct areas based on motion state: main diffusion, random diffusion, and vortex. Notably, spindle speed and feed rate are most influential on the orthogonal diffusion angle of the main diffusion zone, whereas cutting depth most heavily impacts the top view diffusion angle. Chip scattering on the table showed an exponential increase in average chip size with sampling distance, whereas the boundary surface model accurately characterizes chip motion and demonstrates a reasonable degree of reliability, offering potential in predicting chip morphology and diffusion state. This model has important implications for wood milling practices, particularly in controlling chip dispersion.