Toronto, situated at the shore of Lake Ontario, was an isolated city before the arrival of the railways in the 1850s. Three primitive roads connected the city with the rest of the province: Kingston Road went east, the Dundas Highway went west to London, and Yonge Street trailed north to Lake Simcoe. When it rained, all the roads became quagmires. Most people chose to travel by boat, if possible.

York, the name of the original town, was a small ten-block rectangle at the eastern end of the harbour. It extended from Berkeley Street west to George Street and north from Front Street, which ran along the harbour, to Lot or Queen Street. In 1834, York became the city of Toronto. By the 1850s, the city was expanding westwards. The Provincial Parliament and many fine homes were located beyond Yonge Street. Farther to the west, the Garrison Common, a large piece of land used for troop manoeuvres, surrounded Fort York.

Charles Dickens, who visited in the 1840s, wrote in his American Notes that many of Toronto's streets were paved and gas lit. Planked footways along the streets were "kept in very good and clean repair". King Street was known as the best street in the city, and its stores had plate-glass windows. When fire destroyed the area around St. James Cathedral and the Market in 1849, the buildings were rebuilt with brick walls and tin roofs. At the time, the city was able to boast of a town hall, law courts, university and colleges, a Board of Trade, a Mechanics' Institute and public baths.

The Provincial Asylum, the Provincial Parliament, church steeples and the windmill at Gooderham and Worts' mill and distillery were the most visible structures on the low skyline. The well-to-do lived in large houses on spacious lots, many near the harbour. The poor lived in wretched housing and scrambled for a living. Freely available, inexpensive liquor served as an outlet. Sanitation in the city was poor. Sewage and water sources often mingled, and Torontonians suffered through periodic epidemics of typhoid and cholera.

For entertainment, travelling circuses, such as Barnum's, led parades through the city to the Fair Green by the lakeshore. People danced the Elephant Polka and the Grand Trunk Mazurka at charity and military balls. St. Lawrence Hall offered sophisticated activities like the recital of the Swedish Nightingale, Jenny Lind, and lectures by the American abolitionist, Frederick Douglass. In the summertime, horse-ferries went to the Peninsula (Toronto Island) for fishing and picnics. In the winter, ice-boating, skating and fishing were popular pastimes on the frozen harbour.

By the early 1850s, Toronto's population had grown to over 40,000 people. The city was surrounded by small hamlets such as Yorkville, Parkdale, Brockton and Carlton and a more remote hinterland of villages, farms, orchards, and vineyards.

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