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Washingtons Trail 1753 Travel with George Washington through western Pennsylvania Washingtons Trail is a driving route through western Pennsylvania. Traversing modern highways the route commemorates young George Washingtons first military and diplomatic venture in the Fall and Winter 1753 1754. Today the route follows major roads. However in some areas there are alternate historic or scenic routes suggested which may more closely align with Washingtons travel in the Fall of 1753.