John McCutcheon was born in 1874 in Grey Township, Huron County. He was the oldest of five sons born to farmer, William McCutcheon, and his wife Hannah McLennan. In 1887, when John was thirteen, his father gave up farming to become a farm implement salesman and moved his family to Listowel.

In Listowel, John graduated from high school and took his first teaching assignment in Tralee, a small farming community seven miles east of Listowel. In the earliest years, teachers were not required to have professional education – this requirement was only instituted after the Toronto Normal School opened, when it became evident that graduates of the program did superior work as teachers.

In 1903 he married Margaret Welsh, whose father, John, was a farmer near Tralee. Their first child, John Wallace McCutcheon, was born in June of 1905. His birth certificate indicates that the young couple were living on her parents’ farm at the time.

By 1908, John was qualified to teach in the newly built Stratford Normal School located on Water Street. This was one of four Normal Schools constructed by the province at the time to provide education in regular training practices for teachers.

John, his wife, and their young son, moved into 191 Water Street which was also built in 1908. The house was built on land previously owned by W. F. McCulloch; George McLagan, a furniture manufacturer; and James Trow. George McLagan built the house at 210 Water Street which was surrounded by the land from Romeo Street to Front Street and Ontario Street to the river. Present day Trow Avenue was the driveway to the impressive home. James Trow bought the property in 1907 and began to subdivide it into lots.

John McCutcheon was the English Master at the Stratford Normal School from 1908 to 1914. During their stay in Stratford, John and Margaret became the parents of twins, Marjorie Elaine and William Maxwell, who were born in 1910.
The family moved to Toronto at the end of the school year in 1914. There, their second son, David Welsh McCutcheon, was born in 1919.  Sadly, David died six months later in the 1918-1919 pandemic known as the Spanish Influenza at the time.

John continued his education and earned a Doctorate in Pedagogy. He also wrote a book, The Physical Welfare of the School Child. He left teaching and became a Commissioner for the Ontario Provincial Government. In June 1923, he returned to Stratford to partake in a special lecture series at the Normal School with a number of other visiting dignitaries.

Their son, John Wallace became a medical doctor, Marjorie followed in her father’s footsteps as a teacher, and William Maxwell had a career in the army. John McCutcheon died in 1950 and was buried in Mount Pleasant Cemetery in Toronto. Margaret died fifteen years later and is buried alongside John, their infant son, David, and their daughter, Marjorie, who never married.