Route 371 originates as a road cut in 1791 and later used for the Newburgh and Cochecton Turnpike in 1806.
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In 1801, the state legislature of New York and Pennsylvania brought up the proposal for the Newburgh and Cochecton Turnpike (later the Great Bend and Newburgh Turnpike) to connect the Hudson River to the Delaware River.
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There, the route begins to follow the alignment of the Newburgh and Cochecton Turnpike.
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