Estimating the resonant frequency of non-smooth systems with contacting elements is critical for the design, control, and health monitoring of various mechanical and aerospace structures. The nonlinearity caused by the intermittent contact excludes the use of efficient linear methods; hence, predicting vibration characteristics of these systems becomes computationally challenging. Furthermore, several numerical and analytical approaches that have been developed for analyzing smooth nonlinear systems cannot be applied to analyze non-smooth oscillators. To understand the dynamic properties of non-smooth dynamical systems, the bilinear frequency approximation (BFA) method, a classical analytical tool, was developed to estimate the nonlinear natural frequency of bilinear oscillators by using the linear characteristics of underlying linear subsystems to construct a closed-form analytical solution. However, the traditional BFA method is only applicable to systems in which the gap size between the contacting element is zero, which limits the capability of this efficient analytical technique. In this paper, a generalized BFA method is proposed to extend the capability of the method to capture the nonlinear natural frequency of high-dimensional non-smooth systems where either gaps or prestress exist. The generalized BFA method employs the natural frequencies, mode shapes, and modal amplitudes of the linear subsystems as well as the gap size at the contacting degrees of freedom (DOF) to estimate the nonlinear natural frequencies at different amplitude levels. The backbone curve of non-smooth oscillators can be efficiently constructed using the proposed analytical method. The generalized BFA method is demonstrated on a single-DOF system, a three-DOF system, and a finite element model (FEM) of a cantilever plate with contacting elements. The results show that the proposed method provides an accurate approximation of the backbone curve for the first resonance, which has the most dominant vibration response, with very low computational effort, but a rather poor approximation for higher resonances. The proposed technique can be integrated with high-dimensional FEMs to analyze the nonlinear resonance of complex structures. The performance of the method is validated both numerically and experimentally in this work.