College Street takes its name from the University of Toronto, originally King's College. Between Spadina Avenue and Yonge Street, College marks the southern boundary of the original 1827 land grant for the college. The street was immediately proposed as an east-west route along the boundary, although the section was not built until 1859. The first section built was to the west of Spadina Avenue, through the estate of Robert Baldwin, who laid out the route. This section was built with the that was also used for Spadina. The section through Baldwin's estate was laid out in 1842, and the wide section was extended to Manning Avenue through the Denison and Crookshank estates. After John Howard made the 1873 land grant which would become High Park, the Denison family proposed that the city extend College Street west as a sort of 'driving park' to access the new public lands. The path to the west of Manning Avenue was blocked by William Wakefield, who owned the land beyond and was holding out for a high sale price. The purchase of Wakefield's land did not take place until 1879. The right-of-way purchased through Wakefield's land was the standard width, rather than the 100 ft width to the east. The cost of the land may have been a factor. Building the route west of Clinton Street was a challenge in the 1880s. At the time, a direct line west would have traveled through the ravines of Garrison and Brewery Creeks as far as Dufferin Street, the western city limit at the time. Instead, the road was rerouted along a north-western crescent running parallel to the creeks. The route then proceeded straight as far west as Havelock Street, just east of Dufferin. At Havelock Street, the right-of-way intersected the property ofCharles Lindsay. The alignment of College Street would have bisected his property, leaving unsaleable lot sizes on the south side of College. Lindsay was able to convince the city to reroute around his property to the north, with a 'kink' that exists to this day. After the suburb of Brockton was annexed in the 1880s, the final section of College Street was built to Lansdowne Avenue in 1886. It was expected that College would be extended further, but just west of Lansdowne the rail lines created a barrier. A precursor to an extended College Street, called Grenadier Road, was laid out in the Roncesvalles district, and on the west side of High Park in Swansea as well as a section in Etobicoke, but connections to those streets were never made. Streetcar service extended as far west as Dufferin by 1889, and to High Park by 1893. Sunday operation of the line to High Park did not begin until 1897, after a citywide plebiscite was held on the issue of Sunday streetcar operation. The streetcar led to the development of residential sub-divisions on both sides, with street frontages actually empty. The frontages were used for billboards, with development on the street only filling up the lots on both sides by World War I, although some vacant lots existed into the 1920s.
