The commercialization of bioenergy has been significantly limited by various material handling issues due to the poor flowability of granular biomass materials. Addressing these issues demands a fundamental understanding of flow physics and robust models to predict the multi-regime flow behavior of biomass particles. In this study, we investigated the multi-regime flow behavior of loblolly pine chips, a widely used bioenergy feedstock, through combined experiments and simulations. A quasi-static hypoplastic model and a cross-regime Drucker–Prager (DP)-μ(I) model were utilized and validated against inclined plane flow experiments to understand the quasi-static and dense flow behavior of milled pine chips. The results show that along the inclined plane, loblolly pine chips mainly present in heap flow (varying thickness along the plane), and in plane flow (iso-thickness along the plane) only when the inclination closes to the material’s critical state internal friction angle. The results also show that the multi-regime DP-μ(I) model predicts a completely different velocity profile from the hypoplastic model. DP-μ(I) model can capture the flow behavior of pine chips in both flow regimes well but at the cost of extra parameter determination, and the shear-rate dependent rheology model can successfully capture the flow of elongated high-frictional particles. These findings advance the scientific understanding of the multi-regime flow behavior of granular biomass materials and shed light on formulating novel constitutive models to assist granular biomass handling in the bioenergy industry.