In 1848, Ambrose B. White arrived here and established White's Westview Inn, which became a stagecoach stop along the western route for the Butterfield Overland Mail Co. White was elected mayor after the city was incorporated in 1873. Whitesboro is in western Grayson County on U.S. 82 and is one of the gateway cities to recreational activities at Lake Texoma and Lake Ray Roberts. Numerous historical markers are in the area, and bed-and-breakfast accommodations are available.
The annual Peanut Festival, on the third Saturday of October, honors area peanut farmers.