We give ChernWeil definitions of the Maslov indices of bundle pairs over a Riemann surface \Sigma with boundary, which consists of symplectic vector bundle on \Sigma and a Lagrangian subbundle on \Sigma as well as its generalization for transversely intersecting Lagrangian boundary conditions. We discuss their properties and relations to the known topological definitions. As a main application, we extend Maslov index to the case with orbifold interior singularities, via curvature integral, and find also an analogous topological definition in these cases.