Milestoning is a multiscale technique for molecular dynamics (MD) simulation introduced by Ron Elber. The method is based on domain decomposition in molecular state space with direct MD simulation on the micro-scale and a macro-scale kinetic Monte Carlo between the interfaces. These domain boundaries are here called milestones. We analyze this process in a randomized setting with the goal of explaining some observed phenomena, deriving convergence results and suggest some possible improvements and applications.