Henry Shepherd enlisted in 1915 and served overseas during the First World War. He was a decorated soldier and one of only a few Black persons from Peel to serve in a non-segregated unit during the Second World War, fighting with the Lorne Scots Regiment in Brampton.
During the Second World War, he continued to serve with the Lorne Scots and was the first Black Regimental Sergeant Major. In 1944, he was made a member of the Order of the British Empire.
After the war, Henry Shepherd settled in the Georgetown area where he raised a family. During the war, Brampton was his home, which is where the headquarters of the Lorne Scots Regiment is located.
Sadly, Henry Shepherd passed away in 1960, in honour of his service Chapel Street has been ceremonially named as RSM Henry Shepherd Way.