Summary
The first Oriole Station was built in 1906 by the Canadian Northern Railway while its construction was progressing south towards Toronto. Originally, the station was named Duncan after the previous land owner William Duncan. It was a two-storey wood frame structure following a standard “Type 3” design used extensively by the Canadian Northern in rural areas across their system. The second floor would have held the station agent’s living quarters which was a more economical alternative to building separate accommodations. The first revenue train arrived at Oriole in November 1906, but this section of the line had been built separately from the rest of the Canadian Northern system located predominantly in the prairie provinces. Direct service to the west began in 1915 when the last 540 miles from Ruel to Port Arthur was complete.
In 1916, the Canadian Northern built a 2.5-mile connection between Duncan and the Canadian Pacific at Leaside. Initially, this was part of a planned connection to Canadian Pacific’s newly-completed North Toronto Station with the hopes of providing passenger service there. This never came to fruition, and instead the connection was used to reach the Canadian Northern’s Eastern Lines Shops once it was built in 1919. By that point, Canadian Northern was encountering financial issues and as a result had been nationalized by the federal government. It was formally merged into newly-formed Canadian National in 1923, and the station’s name was changed from Duncan to Oriole around the same time.
In 1938, the original Canadian Northern station was replaced by a small shelter used as a train order office and flag stop on the south side of York Mills Road. The original station was moved away from the tracks and converted into a sectionhouse for employees. As the popularity of automobiles increased during the early to mid 20th century, passenger ridership began to decline and service was reduced as a result. A total of seven trains stopped at Oriole per day in 1953, which was reduced to five per day by 1955. That year, the shelter was moved to the north side of York Mills Road. It was closed to passengers by 1960, but continued to function as a train order office until 1978. The original Canadian Northern station remained as a sectionhouse until it was demolished in 1987, at which point in time it was the last example of a Canadian Northern Type 3 station design left in Ontario.
This 1917 aerial photo of a stunt biplane inadvertently captured the original Canadian Northern Duncan Station, seen to the right of the plane. Courtesy of the Ingenium Digital Archives. 
A conductor on a caboose picks up orders from the station agent at the Oriole flag stop in 1955. Photo by Ted Chirnside, courtesy of the Toronto Public Library. 
An alternative view on the same day as the previous photo, this time from the other side of the station showing CNR 4201. Photo by Ted Chirnside, courtesy of the Toronto Public Library. 
Oriole station in 1964 after the implementation of Centralized Traffic Control (CTC). A new signal cantilever has been put into place nearby. Courtesy of the Al Paterson Collection. 
The original Canadian Northern station on an unknown date, from an unknown photographer. Judging by the vehicle on the right, this photo was likely taken during or after the 1970’s. Courtesy of the Toronto Public Library.
Condensed Station Info:
| Location: | Served By: | Current State: | Date Built: | Date Demolished: |
| South of York Mills Road | Canadian Northern (1906 – 1918) Canadian National (1918 – 1960) | Demolished (Both) | 1906 (First) 1938 (Second) | 1987 (First) 1978 (Second) |