Toronto, situated at the northwestern end 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.

Toronto entered the railway era on May 16, 1853 when the engine "Toronto" pulled four passenger cars to Machell's Corners (Aurora). This first trip took about five hours. Beginning at Front and Simcoe Streets near the Provincial Parliament building, the train ran west on track south of Front Street passing Bathurst Street and then curved north. The route's destination, Collingwood, resurrected Lieutenant Governor Simcoe's "Toronto Passage" as a shortcut for western travel. However, the railways' greatest benefit was to permit year round travel on a regular basis.

Toronto was well-situated to take advantage of the railway era with an excellent geographical location for trade. At the end of the 1840s, British trade laws had changed drastically, ending Montreal's export trade monopoly. American and Torontonian commercial drive meant that New York became a valuable market for Toronto. Markets were also developed when railways opened up the area around the city as well.

Railways were enormously expensive to build. The Ontario, Simcoe & Huron (by 1858, renamed the Northern Railway) took eleven years to finance and build the city's first railway. Toronto's second railway, the Grand Trunk Railway was the biggest. The Montreal-based Grand Trunk entered Toronto first with a Toronto-Brampton-Sarnia line in October 1855. Its station was built at the foot of Bathurst Street. The third railway, the American-financed Great Western, came from Hamilton in December 1855 and located its passenger terminal at Bathurst Street, just north of the Grand Trunk's. All three railways built their yards on the western edge of the city on open land, known as the Esplanade. Parliament had deeded this land in 1818 to the citizens of York for their recreational use. The railways eventually occupied all of it.

In 1856, the Grand Trunk Railway's eastern line from Montreal crossed the Don River south of Queen Street. A temporary station was constructed east of the river. The track followed the Don's western bank around Gooderham & Wort's mill, curved around the old Gaol on Parliament Street and crossed the open Fair Green land. Railways need land, and a great deal of it for track, stations and yards. Toronto's problem in the 1850s was that it went to the water's edge. The Front Street shoreline from Berkeley to Bay streets was filled with houses, businesses and wharves. The City and the Grand Trunk Railway wrangled for several years about the solution to this problem. Finally, the railway agreed to create a 100 foot landfill strip across the harbour. Forty feet would be for the railway's use. This landfill was the beginning of the eastern Esplanade.

The Grand Trunk Railway faced two problems. First, the landfill would take months to settle before tracks could be laid. Secondly, the railway had two stations at the city's edges – one at Bathurst Street and the other east of the Don River, but no station in the centre. As a solution, temporary track was laid along the south side of Front Street through the crowded district to west of Bay Street where it joined the Northern Railway track. As all three railways were built to a similar 5'6" track gauge, known as "Provincial Gauge", trains were able to run on each other's lines. A temporary station, adjoining Northern's at Front and Bay Streets was built. As soon as the Esplanade landfill settled, the railway laid track to its western yards. In 1858, the Grand Trunk built the first Union Station just west of the foot of York Street. The two other railways, Northern and Great Western, moved into it closing their own stations. The new station had such amenities as a ladies' waiting room, refreshment room, and barbershop, in addition to ticket, telegraph and baggage offices.

At this time, the largest segment of Toronto's population was Irish. While Toronto's earliest settlers had come mainly from the British Isles or the United States, the Irish potato famine in the 1840s and 50s caused a huge number of poor Irish Catholics to immigrate. These immigrants were one of the first waves that came to Toronto for a new life. The railways and the accompanying industries provided desperately needed jobs for many of these new settlers as they struggled to re-establish their lives. Many lived in houses on the small streets at the eastern end of the city, within easy distance of work at the foundries, breweries and the Grand Trunk's Don Yard. The area became known locally as Corktown.

The physical face of the city began to change. Industrial and residential areas started to separate, at least for the affluent. Railways, because of their own needs and large bulk-carrying capacities, caused manufacturing and heavy industries to concentrate along railway lines. As the number of lines and yards increased, people who could afford to gradually moved away from the waterfront and the noise and dirt of the yards and tracks. Their properties were subdivided into smaller housing lots or became used for commercial and industrial purposes.

A major change for the larger railways in the 1870s was alignment with the narrower American standard gauge track (4 ft. 8 ½ in.). The volume of traffic across the border made it politic to change to the American system. In 1870, the Provincial Gauge was repealed and the railway lines began to switch. The Great Western changed first, followed by the Grand Trunk and last by the Northern Railway, which had the least contact with the United States.

Four new railways, two narrow gauge (3 ft. 6 in.), and two standard gauge were built. Narrow gauge track was cheaper and quicker to lay as there was less rail bed to prepare and was often used for local railways. The Toronto and Nipissing (T&N) was the first public narrow-gauge line in North America. Its yards and terminus were at the foot of Parliament Street, opposite the Gooderham and Worts distillery and mill, which owned it. By adding a third rail between Grand Trunk's wider rails, the line ran east to Scarboro Junction, where it turned north. The railway supplied the distillery and mill with grain and lumber, and opened for business in 1871. Ten years later it was taken over by the Midland Railway, which in turn was taken over by the Grand Trunk Railway in 1883.

The second narrow gauge railway was the Toronto, Grey & Bruce (TG&B). Its terminus was at the foot of Bathurst Street between Front Street and Queen's Wharf. The line, which went northwest eventually reaching Owen Sound, opened for service in 1871. It ran a third rail between Grand Trunk's as far as Weston, where it turned west. The TG&B's first central passenger station was on Front Street, near the Parliament Buildings. Later in 1873, it became a tenant in the second Union Station. The railway suffered from its success. The freight volume was so great that the lightweight engines and cars could not handle the loads. The directors resigned, and operations were turned over to Grand Trunk, which re-gauged and ran the railway until the early 1880s. Then Grand Trunk encountered financial problems of its own, and the TG&B merged with the Ontario and Quebec Railway, a subsidiary of Canadian Pacific Railway (CPR), in 1883.

In 1879, the third railway, the standard gauge Credit Valley, located its Toronto terminus in Parkdale on the northeast corner of Dufferin and King Streets. This railway ran on its own line to West Toronto Junction where it turned west to St. Thomas and Elora. The first section, from Parkdale to Milton opened in 1879. After a battle that went all the way to the Privy Council, Credit Valley won the right to use the Esplanade and by 1880 was running trains into Union Station. The railway was complete by 1881, but the company was nearly bankrupt and Canadian Pacific Railway purchased it. This purchase gave CPR an entry for its passenger trains into Union Station, but trains coming from the east had to go to West Toronto and back down the track five miles into Union station. Eventually in 1892, CPR built a line down the Don River from its main line at Leaside to give it eastern access to the station and the waterfront industrial area.

In 1897, the Toronto, Hamilton and Buffalo (TH&B) railway opened the fourth line. It was built by a consortium of four Canadian and American railways to provide competition to the Grand Trunk Railway route from Toronto-Hamilton-Buffalo. By 1910, a half million people a year would use this line. In 1977, CPR purchased control and ten years later merged the line into CP Rail.

The railway building era was characterized by periods of boom and bust. In the 1880s, Grand Trunk and its new competitor, the Canadian Pacific Railway, took over many of the other railways operating in Ontario. The Grand Trunk absorbed the Great Western in 1882, the Midland in 1883 and the Northern in 1888. The Ontario and Quebec Railway as part of the Canadian Pacific Railway absorbed the Toronto, Grey and Bruce and the Credit Valley in 1883.

One of the greatest benefits from these railways was the creation of markets around the city. The lines also allowed farmers to get their crops to market more swiftly, enabled mail-order business such as Eaton's catalogue, speeded up the delivery of mail, and eased travel for people living in the country.

By the 1870s, the first Union Station, built in 1858, was unable to handle the steadily increasing volume of traffic. Great Western chose to build its own station on Yonge Street. Grand Trunk formed a special company to build a new, grander second Union Station just west of the old one, which opened in 1873. However, after ten years the station required more tracks and a large building on Front Street, due to Toronto's tremendous growth. This station was in use until 1927, when the fourth Union Station opened.

The most lasting event occurred in 1883, when Sandford Fleming's proposal to create a 'standard or railway time' to bring conformity to time, was accepted. This meant fewer missed trains due to discrepancies between local times, which could vary wildly, and railway timetables. On November 30, 1883, the City of Toronto adopted standard time. Sandford Fleming was knighted for his achievement of obtaining consensus among many nations for time standardization.

The last railway line built in the city was the Canadian Northern Railway linking Toronto to Parry Sound in 1906. It came down the west side of the Don River and its two yards were located at Cherry Street and in the Rosedale valley. Complaints about the noise and dirt from the valley caused the railway to move that yard to Leaside in 1919.

In the early part of the century, railway traffic on the Esplanade had become increasingly heavy with numerous freight trains and at least 48 passenger trains every day. All these trains ran at ground level presenting a serious hazard to pedestrians and traffic. The Grand Trunk and Canadian Pacific railways formed a joint company, the Toronto Terminals Railway Company (TTR), to regulate rail traffic along the waterfront and in Union Station. Several railways were also reorganized, and Canadian National Railway (CNR) was formed, acquiring Canadian Northern Railway in 1919 and Grand Trunk Railway in 1923.

During the 1920s, the railways along the waterfront underwent a massive change. The Prince of Wales opened the fourth Union Station in August 1927, although the track area was not yet finished. In this new station, the main passenger hall had a high vaulted ceiling and the train sheds low ceilings, in contrast to the earlier Union Stations where ceilings in the passenger areas were low and lofty in the train sheds. Work also began on the enormous viaduct project to separate the railway tracks from the street traffic. The tracks were raised 18 feet above ground level and all the major streets were bridged. Track was laid farther south on the edge of the waterfront, and the harbour landfill was increased yet again to provide new industrial sites. Both CPR and CNR reorganized and expanded their yards. CPR built the John Street roundhouse and yards in 1927-28, just south of the Sky Dome today.

The Depression caused a large reduction in the amount of passenger railway traffic between Toronto, Montreal and Ottawa. CNR and CPR began to pool their trains between Toronto and Ottawa in 1933, and between Toronto and Montreal in 1934.

King George VI and Queen Elizabeth made a trans-Canada tour by train in 1939, the first visit to Canada by a reigning monarch. They came to Union Station on June 6, 1939. Three months later Canada would be at war. The Second World War created a surge in passenger travel, and the trains had to be lengthened and run in sections.

Railways were extensively and heavily used during the Second World War to transport troops and military supplies. By the end of the war, tracks, trains and cars were old and worn out. Steam engines were gradually replaced by diesels. The Canadian National Railway experimented with diesel engines in 1928, but only started using them as yard switchers in 1946. As the railways changed to diesels, roundhouses were no longer necessary. CNR closed the Danforth Yard and transferred to its marshalling yards at Mimico.

However, the railway era was passing. By the 1950s, the public's fondness for the ease and mobility of cars for personal travel, the use of trucks for freight, and of airplanes for long distance travel meant that the reliance on railways had dwindled significantly. Railways, although vital to the building of Toronto and indeed our country, remained an important but no longer dominant force.

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