'The Junction' was created where four railway lines crossed. Two railways, the Ontario, Simcoe & Huron (later the Northern) and the western Grand Trunk, had built lines through the area between 1853 and 1873. The third, Credit Valley Railway, created a junction in 1879 when its line branched to the west. Canadian Pacific's (CPR) forerunner, the Ontario and Quebec Railway, which constructed a Toronto bypass just north of Dupont Street, completed the final link. Its track crossed all the other tracks. CPR established its Ontario headquarters at The Junction. The huge yard employed 1,000 men and contained track, storage, roundhouses and machine, boiler, erecting, paint, car and woodworking shops. A second yard was later built at Runnymede with workmen's houses built between so the men could walk to either. The passenger station was located at Dundas Street West and Weston Road.

Manufacturers were attracted to The Junction because of its excellent transportation and shipping facilities. Thirty trains a day ran to Toronto from the four railway stations. Foundries, planing mills, wire factories, and industries, such as Wilkinson Plough, Dominion Showcase and the Heintzman Piano Co. began. Other firms came because land, labour and taxes were cheaper. The Vermilyea Corset Factory owned by Madame Vermilyea employed the wives and daughters of the mills and railway workers.

Land speculators quickly realized the potential of The Junction. One, Daniel Clendenan, bought the Carlton Racecourse at Dundas and Keele streets and registered it as a townsite. In 1888, The Junction was a village of 750 people; by 1891 a town with a population of 5,000. The Globe approvingly described Clendenan, West Toronto's first mayor, as an "energetic pushing businessman". The Mayor and Council pushed for utilities and firehalls, as well as schools and libraries. The corner of Dundas and Keele streets was the centre of town with several blocks of large well-built stores. The streets near the railway tracks were filled with a mix of workmen's homes, while southwest of Annette and Quebec streets was an area of larger homes stretching down to High Park. In one year, 600 houses were built with watermains and sidewalks.

The Junction was prone to booms and busts: 1888 to 1890 was a time of prosperity, while the period between 1893 to 1900 was a recession and poverty became widespread. When factories closed and construction stopped because of a worldwide depression, the municipality was unable to assist its citizens because of large civic debt.

As a railway and factory workers' town, The Junction soon had taverns and pubs. By 1903, alcohol was a big problem for families and a public embarrassment for the town – drunks were visible from passing trains. A prohibition movement grew, led by the Women's Christian Temperance Movement. Hotels were denounced as "cesspools of Harlotry, Vice & Iniquity". Things became so boisterous that the town voted to go dry in 1904 and did not repeal this law until 2000, the last area of Toronto to do so.

Although the period before the First World War was a prosperous one, with no employment insurance, welfare or job safety, people worked long ten to twelve hour days, six day a week. In the days before public welfare, groups like the Women's Benevolent Society and the churches worked hard to provide care to the less fortunate. In their free time, people created their own entertainment. As there were two piano manufacturers in The Junction, music was a popular pastime. Railway maintenance workers flooded a rink at Vine Avenue. The Shamrock Lacrosse Club and baseball were very popular. The latter was played on vacant lots, school and church grounds. From 1905 to 1908, games were held at the Athletic Grounds, later the site of the Annette Public Library.

The closing of the stockyards and several industries caused hardship in West Toronto, although it remained a popular place to live. Toronto annexed The Junction in 1909 and gradually the two have grown together. However, like many other self-contained neighbourhoods in Toronto, people retain their community identity and remain very loyal to their neighbourhood.

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