<p>Modeling fracture in geomaterials like rocks having distinct strength and stiffness is complex due to their unique occurrence of crack branching, coalescence, and interaction patterns. Fractures in such materials are often initiated by contact-induced loading conditions, including joint slip, fault activation, and penetration. Accurately capturing the interplay between contact and fracture mechanics remains a challenge for computational modeling of geomaterials. This study investigates this fundamental duality by proposing a coupled Peridynamics-Discrete Element Method (PD-DEM) framework with realistic damage and contact models. First, the peridynamic formulation is extended through the introduction of a Generalized Bond Softening (GBS) model, which enhances the classical bond-based peridynamics by enabling progressive damage nucleation. To incorporate contact mechanics, a non-local mapping of DEM-based contact forces onto the peridynamic discretization is developed using the coarse graining approach. Additionally, the fractal nature of surface roughness is explicitly modeled through the integration of the non-linear rough normal contact law and appropriate tangential frictional contact. The proposed novel framework is comprehensively validated against experiments through a series of flawed and flaw-less Brazilian tests on a range of geomaterials, from stiff rock specimens to relatively weak clay-like rocks. Results demonstrate the ability of the framework to realistically capture the evolution of crack under varying contact and material properties. This study reveals that the surface roughness predominantly governs the highly non-linear fracture behavior observed in brittle rocks, whereas in case of weak clayey materials, the progressive bond-softening mechanism plays a major role in capturing their characteristic fracture evolution.</p>