Derek Boles spent the first several years of his life adjacent to the CPR main line into Montreal’s Windsor Station where he acquired his interest in passenger trains. For many years he was the head of the English department at a Toronto-area high school. Derek was one of the founding members of the Toronto Railway Historical Association and he wrote and lectured extensively on Toronto’s railway heritage. In 2009, Derek’s book titled Toronto’s Railway Heritage was released through Arcadia Publishing.

He coordinated the annual Doors Open event at Union Station and led popular monthly tours of the station until renovations made doing so impossible. He was also the final chair of the Union Station Revitalization Public Advisory Group and consulted with the City-appointed heritage interpretation team for the $795 million revitalization of the station. He completed two terms on the board of Heritage Toronto and was on the committee that prepared historical plaques for the city.

In addition to numerous executive roles, Derek primarily served as chief historian of the Toronto Railway Museum until his passing in 2021. His knowledge of Toronto’s railway history was immense and a great deal of his work can be found on this website and in a variety of other places. These include but are not limited to Canadian Rail, Branchline, CP Tracks, and the scholarly U.S. publication Railroad History. A more detailed obituary can be found here.