A new approach to upscaling two-dimensional fracture network models is proposed for preserving geostatistical and geomechanical characteristics of a smaller-scale “source” fracture pattern. First, the scaling properties of an outcrop system are examined in terms of spatial organization, lengths, connectivity, and normal/shear displacements using fractal geometry and power law relations. The fracture pattern is observed to be nonfractal with the fractal dimension D ≈ 2, while its length distribution tends to follow a power law with the exponent 2 < a < 3. To introduce a realistic distribution of fracture aperture and shear displacement, a geomechanical model using the combined finite-discrete element method captures the response of a fractured rock sample with a domain size L = 2 m under in situ stresses. Next, a novel scheme accommodating discrete-time random walks in recursive self-referencing lattices is developed to nucleate and propagate fractures together with their stress- and scale-dependent attributes into larger domains of up to 54 m × 54 m. The advantages of this approach include preserving the nonplanarity of natural cracks, capturing the existence of long fractures, retaining the realism of variable apertures, and respecting the stress dependency of displacement-length correlations. Hydraulic behavior of multiscale growth realizations is modeled by single-phase flow simulation, where distinct permeability scaling trends are observed for different geomechanical scenarios. A transition zone is identified where flow structure shifts from extremely channeled to distributed as the network scale increases. The results of this paper have implications for upscaling network characteristics for reservoir simulation.