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Highland has succeeded in preserving its heritage by turning historical areas into great outdoor activities. The former Central New England Railway rail bed has been transformed into the Hudson Valley Rail Trail offering visitors the opportunity to hike, bike, ride on horseback, in line skate, cross country ski and snowshoe. The Trail connects Walkway Over the Hudson State Park, the original Poughkeepsie-Highland Railroad Bridge, and Tony Williams Park offering picnic pavilions, basketball, tennis, a playground and so much more.