We show that a uniform probability measure supported on a specific set of piecewise linear loops in a non-trivial free homotopy class in a multi-punctured plane is overwhelmingly concentrated around loops of minimal lengths. Our approach is based on extending Mogulskii's theorem to closed paths, which is a useful result of independent interest. In addition, we show that the above measure can be sampled using standard Markov Chain Monte Carlo techniques, thus providing a simple methods for approximating shortest loops.