Whitesboro (Whitesborough) is on State Highway 56, U.S. highways 377 and 82, State Highway Loop 441, and the tracks of the Missouri, Kansas, and Texas and Texas and Pacific railroads, fifteen miles west of Sherman in extreme west central Grayson County. Although the first settler in the area was Robert Diamond, the arrival of Ambrose B. White and his family in 1848 marked the beginning of the settlement. At this time the area was called Wolfpath. The settlers who came after White chose to live very near one another. The Butterfield Overland Mail route used White's Westview Inn as a stop on its trail from the Mississippi River to the Pacific Coast from 1858 to 1861. Fourteen families lived there by 1861. A post office, under the name Whitesborough, began operations in 1860. After the Civil War residents were attracted to Whitesborough in such numbers that it became a relatively "wide-open" frontier town; female residents were prohibited from leaving their homes on Saturday nights because shootings were so common. Whitesborough was incorporated on June 2, 1873. At that time it had a population of 500, saloons, several stores, and other businesses. By the end of the decade the community had a bank, a newspaper, and train service from the Missouri, Kansas and Texas Railroad, which had extended its tracks to Whitesborough from Denison in 1879. In 1887 local officials reincorporated the town and received a second charter, this time altering the spelling of its name to Whitesboro. By 1900 the population was 1,214, and by 1920 it had increased to 1,810. Surrounded by farms producing cotton, corn, wheat, and oats, and served by two rail lines, by the mid-1920s the town had become a commercial center. Some seventy-five businesses, including three banks, operated in Whitesboro. In addition, the community had a small number of manufacturers, producing such goods as cottonseed oil and bedding. The population of Whitesboro declined slightly during the 1930s and 1940s, no doubt affected by the Great Depression and World War II. The postwar decades brought growth; the town increased from a population of 1,854 and eighty-three businesses in 1957 to 2,985 and 100 businesses by the late 1960s. In the late 1970s Whitesboro had manufacturers of clothing, metal products, and petroleum products. In 1989 it had fifty-eight rated businesses, and in 1990 the population was 3,209. The population reached 3,760 in 2000.