The Butterfield Overland Mail route used White's Westview Inn as the "Diamond Station" on its trail from the Mississippi River to the Pacific Coast from 1858 to 1861.

After the Civil War, Whitesborough grew into a frontier town where female residents were prohibited from leaving their homes on Saturday nights because shootings were so common.

By 1879, it had a bank, a newspaper, and train service from Denison on a line from the Missouri, Kansas and Texas Railroad.

[5] In 1903, racial tensions were high in Whitesboro after an "Anti-White Man's Club" left a note threatening to poison local wells and "foully treat" and murder "some white girl".

[6] Later that year, a black male was held by police for identification following an alleged attempted rape of a white Whitesboro woman.