Whitesboro is a city in Grayson County, Texas, United States. The population was 3,760 at the 2000 census. Whitesboro is named for its founder, Ambrose B. White. It is part of the ShermanDenison Metropolitan Statistical Area. The first settler in the area was Robert Diamond but beginning of the settlement of Wolfpath began with the arrival of Ambrose B. White and his family in 1848. The Butterfield Overland Mail route used White's Westview Inn as its Davidson Station on its trail from the Mississippi River to the Pacific Coast from 1858 to 1861. A Post office, under the name Whitesborough, began operations there in 1860. Prominent Houston attorney Joe Rollins practiced law in Whitesboro in the 1950s.