Modeling soil-tool interaction is essential for equipment design and performance evaluation on soil behavior responses under loading. Computational tools based on particle-based mechanics such as Discrete Element Modeling (DEM) and Smoothed Particle Hydrodynamics (SPH) have potential in modeling large strain soil dynamic behaviors from soil-tool interaction. The objective of this study is to validate the accuracy and robustness of DEM calibration methodology as it relates to soil deformation during cone penetration on varying initial soil relative density. The influence of factors such as DEM material properties and cone to particle size ratio on DEM cone penetration simulation will be investigated. The paper presents a comparison of DEM predicted cone penetration resistance and laboratory measured penetration data on Norfolk sandy loam. Soil mechanical behavior was modeled with Hertz-Mindlin (HM) contact stiffness model and a new coupled frictional law for static and rolling resistance coefficients. The DEM material properties were calibrated using residual strength from direct shear test. DEM simulations were performed using LIGGGHTS, open source DEM code. Cone penetrometer experiments using anÂASABE standard cone with 12.53 mm cone base diameter and 30-degree cone tip were used to validate the calibrated DEM model. DEM prediction of cone penetration resistance trend and steady state values were in close agreement with the laboratory measured data for relative density range from 5 to 30%. At higher dense states (relative density of 90%), DEM calibration requires further improvement.