The Town of Stonewall was founded in 1878 by Samuel Jacob Jackson. Mr. Jackson was born in Ireland in 1848. As a young child he came to Canada and eventually settled in Ontario.  In 1871, he was a member of a survey crew which came to the Rockwood area where he was to eventually make his home. Mr. Jackson was not only to become a prominent businessman and landowner in the area, he also became a well known and respected politician. He was Speaker of the House from 1891-1895 and was one of only a select few to be given the Speaker's Chair upon retirement. He was also elected to the House of Commons in 1904 and served as Selkirk M.P. until 1908.

Local tradition has it that Mr. Jackson was given the nickname Stonewall for his affinity with the American confederate general of the same name. Mr. Jackson then decided to pass the name on to the new town, and that is how the town in its own way came to be named after its original founder, Samuel Jackson also known to some as Stonewall Jackson.