Summary
Tracks were first laid through what is now Leaside in 1884 by the Ontario & Quebec Railway, which existed solely on paper as a proxy of the Canadian Pacific Railway. Leaside Station was built ten years later after Canadian Pacific completed its Don Branch between Leaside and The Esplanade. The station was originally going to be called East Toronto Junction until the death of William Lea, the property owner who sold his land to Canadian Pacific ten years earlier. The station building itself was a small wooden building with a hipped roof and a long canopy extending outward from the north side of the building. Its design was unique compared to other stations built on the Ontario & Quebec line.
Rail traffic on the O&Q increased rapidly in the decades after it was built. An 1898 proposal suggested laying a second track along the entire Canadian Pacific mainline between Montreal and Windsor to ease congestion, though this would only be partially achieved. The Don Branch was single track and required an Electric Staff Block system between Leaside and Don Station to prevent opposing trains from colliding with one another. This required an Electric Staff machine to be placed in both stations until the implementation of Centralized Traffic Control in the 1960’s. Leaside Yard began to grow around the station in the early 20th Century, mostly for interchange with a connection to Canadian National located about two kilometers to the east. Leaside Station suffered a devastating fire in 1945 that rendered the building unsalvageable. A larger replacement was complete in November 1946, a modern single-storey building with some elements of art deco in its design. It was one of a handful of modern stations built by Canadian Pacific during the postwar era across their system.
The popularization of automobiles began to affect ridership at the new Leaside station within a few years of its completion. Service was gradually reduced until only the Budd cars between Toronto and Havelock stopped at it. The station was closed to passengers in 1975, but was readapted by Canadian Pacific into the Village Station Restaurant. It was to be the first of a planned series of railway-themed restaurants operated by Canadian Pacific’s Hotels Division. The station building was heavily remodeled and a number of historic passenger cars were moved to the property and incorporated into the décor. Unfortunately, the restaurant wasn’t profitable and it closed after eight years of operation in 1983. The building changed hands a number of times, even becoming a CP Police headquarters for a time, but it was ultimately abandoned. The structure was torn down in September 2022 to make way for construction of the Ontario Line subway.
An official company photo of Leaside station in 1899, just five years after its construction. Photo by J. W. Heckman, courtesy of the Canadian Railway Historical Association. 
A 1924 fire insurance map showing Leaside station towards the top right. The north end of the Don Branch can be seen curving south at bottom. Courtesy of Goad’s Atlas. 
A closeup photo of Leaside station in 1945, not long before its destruction. Photo by George Horner. 
A 1955 photo of the new station in its heyday. In the background is the Leaside transformer station, which still exists. Courtesy of the Toronto Public Library. 
A photo of the former Leaside Station as it looked during the 2000’s and 2010’s, up until its demolition.
Condensed Station Info:
| Location: | Served By: | Current State: | Date Built: | Date Demolished/Burned: |
| Village Station Road and Millwood Road | Canadian Pacific Railway (1894 – 1975) | Demolished | 1894 (First) 1946 (Second) | 1945 (First) 2022 (Second) |