James Wilson was born September 21, 1829 in Edinburgh, Scotland, the eldest of five children born to James Wilson Sr., a clerk, and Agnes Roy. In 1850 James Jr. was listed as an engineer fitter (a mechanic who assembles or repairs engine parts).

James emigrated to Canada before September 12,1853, when in Montreal he married Agnes Dale (born around 1830), who was also from Scotland and had recently arrived in Montreal. The newly married couple then moved to Williamsburgh Township, Dundas County (currently Stormont, Dundas & Glengarry United Counties), Canada West, where they had three children: James (1854-1927), Agnes Theresa (1857-1954), and Robert Dale (1859-1938).

It appears that James’ wife, Agnes, died during or shortly after the birth of their third child, because in November 1860 James married Ellen Craig, a resident of Williamsburgh Township. Ellen was born in nearby Charlottenburgh Township and was the daughter of John Craig, a Scottish immigrant, and Mary Westley, born in Lanark County to American immigrants. By 1861 James, his new wife, and his three children had moved to Kingston where James was listed as a mechanic.

By 1871 James and his family were living in Thurlow Township, Hastings County, near Belleville, where James worked as a machinist, probably on the trains. While living there James and Ellen had five children: Mary Jane (1863-1891), Flora Isabella (1866-1912), John Craig (1867-1888), Alexander (1868-1952), and William Waugh (1871-1916). James’ father was also living with them at this time.

James, Ellen, and the children moved to Stratford some time around 1872 when the new locomotive shops were built. Over the years while living in Stratford, James was listed as a fitter or machinist at the Grand Trunk Railway, a position he held until his retirement in 1907 or 1908.

The house at what is now 103 Milton Street was built in 1872/1873, and there were ten family members who lived there at that time.  While in Stratford James and Ellen had three more children: Christina Waugh (1874-1930), Thornton Charles (1877/78-1952), and Alberta Edith Janet (1882-1969)).

Ellen died in Stratford on April 14, 1909. It appears that James lived at 103 Milton until his death from pneumonia on March 16, 1914. Both Ellen and James are buried in Avondale Cemetery. They had seven grandchildren.

Like their father, many of the sons worked for the railways. James Jr. was listed in Stratford as working for the GTR or as a machinist, moving to Kenora in 1903 to work as a machinist in the CPR shops. Alexander worked as a machinist for the GTR in Stratford. William Waugh was also a fitter or machinist with the GTR, moving to Windsor in 1914-1915 to continue his trade. Thornton Charles started his railway career as a fireman with the GTR in Stratford, eventually becoming a railway engineer living in Ottawa.

John Craig and Mary Jane both died in their 20s and were buried with their parents. Agnes Theresa, Flora Isabella, and Alberta Edith Janet all stayed in Stratford. Christina Waugh eventually moved to St. Thomas. Robert Dale lived in Stratford for much of his adult life, and unlike his brothers did not work for the GTR but was a plasterer.