Woodsboro was laid out in late 1906 as a land development project of W.C. Johnson and George P. Pugh of Danville, Illinois, along the St. Louis, Brownsville and Mexico Railway. A post office was established in the Bonnie View Land Company Hotel in 1907, and the town was named for Captain Tobias D. Wood, who had sold his Bonnie View Ranch to Johnson and Pugh. A public square was included in the official town plat in 1908, and it became the center of the economic growth and civic enterprises that characterized Woodsboro's early development. The Woodsboro Commercial Club was founded in 1914, and among its more lasting contributions was a waterworks installed in the town square. The town was incorporated in 1929, and the plaza remains a center for civic activities in Woodsboro.