Early Settlement in "Muddy York"

Over the past 15 millennia, the Huron-Wendat and Petun First Nations, the Seneca, and most recently, the Mississaugas of the Credit River have farmed, hunted, and lived in what is now Toronto. It wasn’t until 1720 that the French established the first trading post along the Toronto Passage to intercept the furs that were being taken across Lake Ontario to New York State by English rivals. Fort Rouillé, built on the site of today’s Canadian National Exhibition (CNE) grounds, replaced the trading post in 1751. When the 1763 Treaty of Paris ended the Anglo-French War after the fall of Québec, French rule in North America effectively ended, and the city’s French antecedents were all but forgotten.

Turrono Today, Tkaronto Yesterday: The name Toronto comes from the Mohawk word tkaronto, which means “trees standing in water.” Tkaronto referred to the narrows that connect lakes Couchiching and Simcoe, located 125km (78 miles) north of the present-day city. There, people fished using fishing weirs (made from stakes driven into the riverbed). In 1680, poor French cartography changed the name to Taronto and applied it to a nearby lake. Over the following centuries, the name was carried south down the portage routes and was ultimately applied to, what is today, the Humber River. The Passage de Taronto became the route that connected Lake Ontario with Lake Simcoe, and the French fort at the mouth of the Humber was named Fort Toronto. Today, you can tell a true Torontonian by how they swallow the middle of the Toronto. They all live in Turrono, not Toronto.

In the wake of the American Revolution, the Loyalists fled north, and the British decided it was time to carve a capital city out of the northern wilderness. Before any forts were built, the British needed to purchase the Toronto lands from the Mississaugas of New Credit. In 1787 the Crown purchased an area stretching from the Humber to the Don River along Lake Ontario for £1,700, 24 lace hats, 120 mirrors, some flannel, 96 gallons of rum, and sundry other trade items. The Toronto Purchase—deemed by the Mississaugas to be a land lease and not a purchase—remained in dispute for 223 years and was settled only in 2010.

In 1791, the British established Upper Canada (modern-day Ontario) as a province. Its first lieutenant governor, John Graves Simcoe, made Toronto its capital and renamed it “York” in honor of Frederick, Duke of York (one of George III’s sons). Simcoe ordered a garrison built and laid out in a 10-block rectangle around Adelaide, Front, George, and Berkeley streets. The land from Queen to Bloor was parceled out to government officials in an effort to mollify the Brits, who resented having to move to the mosquito-plagued, marshy outpost. York was notorious for its always-muddy streets, earning it the nickname “Muddy York.”

By 1795, the hamlet had grown, and the first parliament buildings were erected. Simcoe also surveyed Yonge Street, which would eventually become the longest street in the world. The second Parliament meeting confirmed York as the capital of Upper Canada.

Muddy York: "Muddy York" was a subject of continuous complaint by early settlers. Just how muddy was the early settlement? One apocryphal story tells of a man who saw a hat lying in the middle of a street and went to pick it up. When he did, he found the head of a live man submerged in the muck below.

The War of 1812 & Its Aftermath

When America declared war on Britain in the War of 1812, President James Madison assumed that invading and holding Canada would be a simple matter. The opposite proved to be true. In April 1813, 2,700 American troops on 14 ships and schooners invaded York (population 625), looting and destroying the parliament buildings, the Fort York garrison, and much of the settlement. It was a pyrrhic victory: The Americans suffered heavy losses and failed to take any additional Canadian territory. In retaliation, British troops marched on Washington, D.C., in 1814 and burned all government buildings, including the White House.

Perhaps unsurprisingly, given the events of the war, York’s ruling oligarchy shared a conservative pro-British outlook. Called the Family Compact, the group consisted of William Jarvis, a New England Loyalist who became provincial secretary; John Beverley Robinson, son of a Virginia Loyalist, who became attorney general at age 21 and, later, chief justice of Upper Canada; and Scottish-educated John Strachan, a schoolmaster who became an Anglican rector and, eventually, the most powerful figure in York. Anglo-Irish Dr. William Warren Baldwin, doctor, lawyer, architect, judge, and politician, laid out Spadina Avenue as a thoroughfare leading to his country house; the Boultons were prominent lawyers, judges, and politicians—Judge D’Arcy Boulton built a mansion, the Grange, which later became the core of the Art Gallery of Ontario and still stands today.

The Early 1800s Rebellion & Immigration

In 1834, the city was incorporated, and York became Toronto, a city bounded by Parliament Street to the east, Bathurst Street to the west, the lakefront to the south, and 400 yards north of Queen Street (then called Lot) to the north. Outside this area—west to Dufferin Street, east to the Don River, and north to Bloor Street—laid the “liberties,” out of which the city would later carve new wards. North of Bloor, local brewer Joseph Bloor and Sheriff William Jarvis were already drawing up plans for the village of Yorkville. In 1827, the first university, then called Kings College (later renamed the University of Toronto), opened. This was an intellectual achievement but also an aesthetic one, as the university added new and beautiful architecture.

As increasing numbers of immigrants arrived, demands arose for democracy and reform. Among the reformers were such leaders as Francis Collins, who launched the radical paper Canadian Freeman in 1825; lawyer and attorney general William Draper; and, most famous of all, fiery William Lyon Mackenzie, who was elected Toronto’s first mayor in 1834.

The Toronto Rebellion:  William Lyon Mackenzie, Toronto’s first mayor, founded the Colonial Advocate newspaper to crusade against the narrow-minded Family Compact, the city's ruling group of oligarchs, calling for reform and challenging their power to such an extent that some of them broke into his office and wrecked presses before throwing his type into the lake. By 1837, Mackenzie, undaunted, was calling for open rebellion. The city’s financial turmoil in the wake of some bank failures made his wish come true. On December 5, 1837, a few hundred rebels—armed mostly with pitchforks, pikes, and cudgels—gathered at Montgomery’s Tavern outside the city (near modern-day Eglinton Ave.). Led by Mackenzie on a white horse, they marched on the city. But Sheriff Jarvis was waiting for them, and his militia crushed the rebellion. Mackenzie fled to the United States, but two other rebellion leaders were hanged (their graves are in the Toronto Necropolis). Mackenzie was later pardoned, returned to Toronto in 1849, and was elected to the Upper Canada legislature.

More than anything else, immigration was changing Toronto. During the 1820s, 1830s, and 1840s, immigrants—Irish Protestants and Catholics, Scots, Presbyterians, Methodists, and other nonconformists—arrived in droves. Slavery was outlawed throughout the British Empire in 1833; by the 1840s, roughly 3% of Toronto’s population was black. But the biggest change was the arrival of the Irish. In early 1847, Toronto’s population stood at 20,000. That summer 38,560 Irish immigrants fleeing the Great Famine landed in Toronto, forever changing the city.

Canadian Confederation & the Late Victorian Era

During the 1850s, the building of the railroads accelerated Toronto’s booming economy. By 1860, it was the trading hub for lumber and grain imports and exports. Merchant empires were founded, railroad magnates emerged, and institutions such as the Bank of Toronto were established. The foundations of an industrial city were laid: Toronto gained a waterworks, gas street lamps, and public transportation.

Despite its wealth, Toronto lagged behind Montréal, which had more than double Toronto’s population in 1861. But under the Confederation of 1867, the city was guaranteed an advantage: As the capital of the newly created Ontario province, Toronto, in effect, controlled the minerals and timber of the north.

By 1891, Toronto’s population had reached 181,000. The business of the city was business, and amassing wealth the pastime of such figures as Henry Pellatt, stockbroker and builder of Casa Loma; financier E. B. Osler; senator and president of the Bank of Commerce George Albertus Cox; and investment dealer Alfred Ernest Ames.

The boom spurred new commercial and residential construction. Projects included the first skyscrapers, such as the Board of Trade Building (1892) at Yonge and Front streets; George Gooderham’s Romanesque-style mansion (1892) at St. George and Bloor streets (now the York Club); the Ontario Legislative Building in Queen’s Park (1893); and the city hall (1899) at Queen and Bay streets. In the 1890s, electric lights, telephones, and electric streetcars—replacing their horse-drawn predecessors—appeared.

From Boomtown to the Great Depression

The Great Fire of 1904 destroyed 100 buildings, wreaking more than C$10 million (in 1904 dollars) in damage. Miraculously, no one died in the fire, the cause of which was never discovered.

Between 1901 and 1921, Toronto’s population more than doubled to 521,893. The economy continued to expand, fueled by lumber, milling, mining, manufacturing, and, after 1911, hydroelectric power. Much of the new wealth went into construction, and three impressive buildings from this era can still be seen today: the Horticultural Building at the Exhibition Grounds (1907), the King Edward Hotel (1903), and Union Station (1914–20).

The booming economy and its factories attracted a wave of new immigrants—mostly Italians and Jews from Russia and Eastern Europe—who settled in the city’s emerging ethnic enclaves. By 1912, Kensington Market was well-established, and the garment center and Jewish community were firmly ensconced around King Street and Spadina Avenue. Little Italy clustered around College and Grace streets. By 1911, some 30,000 Torontonians were foreign-born, and the slow march to change the English character of the city had begun.

"Toronto the Good": Toronto’s reputation for conservatism was well deserved. While the city was blessed with many beautiful churches, its nickname, “Toronto the Good,” had less to do with religion and more to do with legislation against fun. This was, after all, the city that, in 1912, banned tobogganing on Sunday. As late as 1936, 24 men were arrested during a heat wave for exposing their chests…at the public city beaches! (At the time, the law stated that bathing suits were to cover men from neck to knees.) In 1947, cocktail lounges were approved, but it wasn’t until 1950 that playing sports on Sunday became legal. Leopold Infeld, a University of Toronto physicist who worked with Einstein, famously said: “I dreaded the Sundays and prayed to God that if he chose for me to die in Toronto he would let it be on a Saturday afternoon to save me from one more Toronto Sunday.”

As it became larger and wealthier, Toronto also became an intellectual and cultural magnet. Artists such as Charles Jefferys, J. E. H. MacDonald, Arthur Lismer, Tom Thomson, Lawren Harris, Frederick Varley, and A. Y. Jackson, most associated with the Group of Seven, set up studios in Toronto. Their first group show opened in 1920. Toronto also became the nation's English-language publishing center, and national magazines such as Saturday Night (1887) and Maclean’s (1905) were launched. The Art Gallery of Ontario, the Royal Ontario Museum, and the Royal Alexandra Theatre all opened before 1914.

Women advanced, too, at the turn of the 20th century. In 1875, Jennie Kidd Trout became the first Canadian woman authorized to practice medicine. Trout was joined 5 years later by suffragette Emily Stowe, who obtained her medical license in 1880. In 1884, the University of Toronto began to accept women. The women’s suffrage movement gained strength, led by Dr. Stowe, Flora McDonald Denison, and the Women’s Christian Temperance Union.

But increased industrialization brought social problems as well, largely concentrated in Cabbagetown and the Ward, a large area that stretched west of Yonge Street and north of Queen Street. Here, people lived in crowded, wretched conditions: Housing was inadequate; health conditions were poor; and rag-picking, or sweatshop labor, was the only employment.

When Britain entered World War I, Canada was immediately pulled into it. Toronto became Canada’s chief aviation center; factories, shipyards, and power facilities expanded to meet the needs of war; and women entered the workforce in great numbers.

The 1920s roared along, fueled by a mining boom that saw Bay Street become a veritable gold-rush alley. Then the Great Depression hit, and the only distraction from its bleakness was the opening of Maple Leaf Gardens in 1931. Besides being an ice-hockey center, it was host to large protest rallies during the Depression; later, it welcomed anyone, from the Jehovah’s Witnesses to the Ringling Bros. Circus and the Metropolitan Opera.

As in the United States, hostility toward new immigrants was rife during the ’20s. It reached a peak in 1923, when the Chinese Exclusion Act was passed, which banned Chinese immigration. In the 1930s, anti-Semitism intensified (Canada accepted only 4,000 Jewish refugees out of the 800,000 seeking asylum). In August 1933, the display of a swastika at Christie Pits Park caused a battle between Nazis and Jewish men, who had been playing baseball before the riot broke out. As if things weren’t bad enough, a polio epidemic struck in 1936.

World War II & Aftermath

Unlike World War I, Canada wasn’t automatically bound to enter World War II by Britain’s declaration of war. However, when the Canadian Parliament voted to declare war on Germany on September 10, 1939, the move was widely supported by Canadians.

The Second World War brought new life to Toronto—literally. Toronto men rushed to volunteer to serve while women took their place in the factories. Once again, the city became a major aviation center.

After World War II, prosperous Toronto continued to expand, especially into the suburbs. By the 1950s, the urban area had grown so large, disputes between city and suburbs were so frequent, and the need for social and other services was so great, that an effective administrative solution was needed. In 1953, the Metro Council, composed of equal numbers of representatives from the city and the suburbs, was established. 

Mid- & Late 20th Century

Toronto became a major city in the 1950s, with the Metro Council providing a structure for planning and growth. The Yonge subway opened, and a network of highways was constructed. It linked the city to the affluent suburbs. Don Mills, the first postwar planned community, was built between 1952 and 1965; Yorkdale Centre, a mammoth shopping center, followed in 1964. American companies began locating branch plants in the area, fueling much of the growth.

The city also began to loosen up. While the old social elite continued to dominate the boardrooms, politics, at least, had become more accessible and fluid. In 1955, Nathan Phillips became the city's first Jewish mayor. In 1947, the Chinese Exclusion Act of 1923 was repealed. And after 1950, Germans and Italians were allowed to enter once again. Then, under pressure from the United Nations, people from Hungary, Yugoslavia, Portugal, and Greece poured in. Most arrived at Union Station, having journeyed from the ports of Halifax, Québec City, and Montréal. The 1960s brought an even richer mix of people—West Indians, South Asians, refugees from Chile, Vietnam, and elsewhere—changing the city’s character forever.

In the 1960s, the focus shifted from the suburbs to the city. People moved back downtown, renovating the handsome brick Victorians so characteristic of today’s downtown. Yorkville emerged briefly as the capital of hippiedom—the Haight-Ashbury of Canada. Gordon Lightfoot and Joni Mitchell sang in the coffeehouses, and a group called the Toronto Anti-Draft Programme helped many Americans fleeing the Vietnam War Draft settle in Toronto.

Montréal's Loss, Toronto's Gain: In the 1970s, Toronto became the fastest-growing city in North America. For years, it had competed with Montréal for first-city status, but it was the election of the separatist Parti Québécois, in 1976, that boosted Toronto over the top. Montréal's loss was Toronto's gain, as English-speaking families and large companies chose Toronto over French-speaking Québec. The city overtook Montréal as a financial center, boasting more corporate headquarters. Its stock market was more important, and it remained the country's prime publishing center.

During the 1970s, the provincial government also helped develop attractions that would polish Toronto’s patina and lure visitors, including Ontario Place (1971) and the Metro Zoo (1974). The CN Tower is another development from that era, and for more than 3 decades, it was the tallest free-standing structure in the world (now surpassed by the Burj Khalifa in Dubai). Unfortunately, in spite of strong efforts by preservationists, Toronto lost many historic buildings in the 1960s and ’70s.

The 1980s were an interesting time in Toronto. On the one hand, the city fell into the habit of conspicuous consumption that seemed to define the oft-mocked era. Yorkville was transformed from hippie-coffeehouse central into a hive of chic boutiques. On a more positive note, previously neglected neighborhoods such as the Annex and Cabbagetown were revitalized, the grand mansions brought back to life by new waves of residents. People began to appreciate Toronto’s historic architecture, working to restore it rather than tear it down as they had in the 1970s. The Elgin and Winter Garden theaters were fully renovated and reopened, as was the Pantages Theatre (now the Ed Mirvish Theatre). In 1986, Toronto’s Mirvish family (of “Honest Ed’s” fame) created Mirvish Productions, which (along with the now-defunct Livent group) ushered in a renaissance on the Toronto theater scene. There was also important new construction in the city: The Roy Thomson Hall opened in 1982, and SkyDome (now the Rogers Centre) debuted in 1989.

In the 1990s, the Greater Toronto Area (GTA) really began to boom, fueled in part by rising immigration to the city. In 1998, a megacity merger forced the former city of Toronto into a union with five previously independent boroughs, causing cuts in public services as the provincial government off-loaded transit and welfare costs to the city. 

The 21st Century

The new century began with a renewal of the city's cultural inventory. At long last, the city got a purpose-built opera house, the Four Seasons Centre for the Performing Arts, which opened in 2006. Also, the Royal Ontario Museum, the Art Gallery of Ontario, the Ontario Science Centre, the Royal Conservatory of Music, the National Ballet School, and the Gardiner Museum of Ceramic Art all underwent extensive renovations.

By 2008, Toronto had become North America’s largest condo market, with towers going up all over the city. The trend continues unabated, and Toronto’s future seems destined to become a city of high-rise living. In 2017, the market reached a new extreme: C$31 million for a penthouse suite in the Four Seasons hotel/condo tower.

Also on the rise are long-overdue efforts to reclaim the city's waterfront, where hotels, stadiums and theaters, bars, restaurants, and parks are being developed, including the whimsical and attractive Sugar Beach, at the foot of Jarvis Street (a reference to the Redpath sugar refinery, one of the last remaining industrial uses on the waterfront). There is no access to the lake from this beach, but a new boardwalk heads east to this burgeoning new East Bayfront neighborhood. The expansive Sherbourne Common is a welcome addition of green space on the site of a former industrial area—plus it claims to be the first park in Canada with a neighborhood-wide stormwater treatment facility as an integral part of its design. Even the Don River’s banks have been rehabilitated, with trails to explore by foot or bike. Farther west, an old Ontario Place parking lot has been transformed into a lush, shoreline-hugging oasis called Trillium Park. The newly landscaped rolling hills are planted with dozens of native flowers and trees that hide serpentine paths that connect back to the main waterfront, the Martin Goodman Trail.

As the city grows, preservationists are stepping up to breathe life into Toronto's abandoned or derelict heritage structures. Three recent additions bridge past and present. Artscape Wychwood Barns is an artists' colony and local food resource center fashioned from streetcar repair barns from the 1920s. The Toronto Railway Museum, just a fly ball away from the Rogers Centre, is set in an old railroad roundhouse. And Evergreen Brick Works has transformed a quarry into a center for sustainable living.

Toronto continues to be very much a work in progress. As the skyline becomes more crowded, there’s a noticeable increase in street life and energy as these rising condos fill up. The city's embrace of diverse and cosmopolitan cultures has helped shape what has become a dynamic and ever-changing scene.

Ontario Legalizes Recreational Pot: In 2018, Ontario legalized recreational marijuana. Those 19 years of age and older can now smoke weed wherever tobacco smoking is permitted (this limits you to public places, private residences, and designated smoking hotel rooms). In Toronto, smoking isn’t allowed in parks or on patios, and you could face serious fines if caught.

These days, the Province has become the biggest pot dealer in town. Ontarians get weed delivered right to their homes by placing orders on the online-only Ontario Cannabis Store, which was the only place to buy weed legally at the time of legalization. As of April 2019, however, private pot retailers are now licensed to operate legally.

Prior to legalization, Toronto already had dozens of pot shops sprinkled about selling fancy toking devices, esoteric weed strains, and other Mary Jane–laced goodies, including chocolates, gummies, and more. Despite the city’s old moniker, Toronto the Good, this town has been flouting the pot-smoking rules for years. Legalization just means that the variety and quantity of Amsterdam-like cafes will increase over the coming years.

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.