Particle crushing occurs near the tip of a penetrometer and influences the development of the tip resistance. To study particle crushing near a penetrometer tip, a cone penetrometer was monotonically jacked and then load-tested in medium dense and dense silica sand samples prepared in a half-cylindrical calibration chamber with viewing windows. During the tests, images of the advancing penetrometer and the surrounding soil were taken using digital cameras and analyzed to obtain the displacement and strain fields around the penetrometer using the Digital Image Correlation (DIC) technique. Subsequently, soil samples were collected near the tip of the penetrometer using a novel agar-impregnation technique and digitized using an X-ray microscope. The digitized samples were analyzed to reconstruct the three-dimensional models of individual particles, generating the gradation and relative breakage parameters of the sand around the cone penetrometer.