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In 1787, Nathaniel Gordon purchased 1,350 acres (5.46 square km) of land, then known as "Newville," from a cousin of President James Madison. In 1794, or perhaps earlier, Gordon applied for and was granted a license to operate a tavern there, which, as was typical of the time, was used as a place to eat, lodge and discuss local matters. It sat at the intersection of two highways: "The Fredericksburgh Great Road," a stage route from Charlottesville, through Orange, to Fredericksburg; and "The Richmond Road," which led from the Virginia capital, through Louisa, west over the Blue Ridge Mountains into the Shenandoah Valley. President Thomas Jefferson described the tavern in 1802 as a "good house" when recommending the best route south to Charlottesville from the recently established national capital on the Potomac. The building was known as Gordon's Tavern, Gordon Tavern and later as Gordon Inn.