Today, it’s hard to believe that a “horse car” and streetcar route used to bisect the neighbourhood – but from 1881 to 1930 the Winchester Streetcar did just that. This route would connect riders to the Winchester Street Bridge that crossed the Don River.
From Transit Toronto (transit.toronto.on.ca)
July 26, 1881
Service begins on a new horse car route called WINCHESTER, running from Front and York via east on Front, north on Church, east on King, north on Sherbourne, east on Carlton, north on Parliament and east on Winchester to Sumach Street. The service features a short stretch of single track operation in the easternmost few-hundred feet of Winchester.
According to this timeline, the route experienced many changes (not the least of which was going from horse to electric power).
This photo from July 27, 1923 shows workers on Winchester Street looking westward to Sackville Street.
This is an image of one of the streetcars in 1921 at Queen Street and Church Street.