The land forming the settlement of this pretty village was squatted on in 1853 by John Shennan, who built a saw and grist mill. Before the project was complete, he sold out to David Pinkerton. In 1856, a log school was built and in 1860 a post office opened. Matthew Pinkerton was postmaster from 1860 until 1866. One of the most famous Pinkerton residents was Senator J. J. Donnelly, who was also Reeve of the Township in 1897 and 1898.At the turn of the 20th century there were many thriving businesses in Pinkerton, including a wagon and tinsmith shop, blacksmith, saw mill, grist and flour mill, and a shingle mill. A hotel opened in 1861, and was destroyed by fire on Good Friday in 1971. As of this date, the grist mill continues to operate, still powered by the Teeswater River.