The existence of bedding planes in natural shale formations makes the fracture characterization remarkably complicated. To achieve a further understanding of the anisotropic crack extension behaviors of shale using a linear elastic fracture mechanics approach, four groups of three-point bending tests on Longmaxi shale from southeast Chongqing were conducted in this study with different bedding plane inclination angles. The fracture propagation paths were observed using a scanning electron microscope. The results indicated that cracks initiated along the bedding plane when the bedding plane inclination angle (i.e., the angle between the loading direction and the normal direction of the bedding plane) was relatively large; in contrast, cracks penetrated into the matrix and induced higher fracture toughness in cases with lower bedding plane inclination angle. Brittle fractures occurred in the tested shale, and the fracture strength was strongly dependent on the bedding plane inclination angle. Meanwhile, the stress field around the crack tip was analyzed theoretically. The results indicated that the crack tip stress field of anisotropic shale is not only determined by the stress intensity factor but also related to the elastic constants and bedding plane inclination angle. Furthermore, a criterion for determining whether a crack extends along the bedding plane was developed by distinguishing the differences in the strengths of the shale bedding and the matrix.