We show that a uniform probability measure supported on a specific set of piecewise linear loops in a nontrivial 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 method for approximating shortest loops.
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