York, Upper Canada in the context of "Toronto"

Front Street is an east–west road in Toronto, Ontario, Canada. First laid out in 1796, the street is one of the original streets of the Town of York. The street was laid out along the shoreline of Lake Ontario as it existed during that time. It remains an important street with many important landmarks, including the St. Lawrence Market, Meridian Hall, Union Station, and the Metro Toronto Convention Centre. The eastern section of Front Street, in the West Don Lands, east of Cherry Street, is being rebuilt as a broad tree-lined boulevard, intended to be the pedestrian-friendly commercial spine of the new neighbourhood.

43°39′09″N 79°22′54″W / 43.65250°N 79.38167°W / 43.65250; -79.38167

The Battle of York was a War of 1812 battle fought in York, Upper Canada (today's Toronto, Ontario, Canada) on April 27, 1813. An American force, supported by a naval flotilla, landed on the western lakeshore and captured the provincial capital after defeating an outnumbered force of regulars, militia and Ojibwe natives under the command of Major General Roger Hale Sheaffe, the Lieutenant Governor of Upper Canada.

The name of Toronto has a history distinct from that of the city itself. Originally, the term "Tkaronto" referred to a channel of water between Lake Simcoe and Lake Couchiching, at what is now the city of Orillia, on maps as early as 1675 but in time the name passed southward, and was eventually applied to a new fort at the mouth of the Humber River. Fort Toronto was the first European settlement in the area, and lent its name to what became the city of Toronto.

John Graves Simcoe identified the area as a strategic location to base a new capital for Upper Canada, believing Newark to be susceptible to American invasion. A garrison was established at Garrison Creek, on the western entrance to the docks of Toronto Harbour, in 1793; this later became Fort York. The settlement it defended was renamed York on August 26, 1793, as Simcoe favoured English names over those of First Nations languages, in honour of Prince Frederick, Duke of York. Residents petitioned to change the name back to Toronto, and in 1834 the city was incorporated with its original name. The name York lived on through the name of York County (which was later split into Metropolitan Toronto and York Region), and continues to live on through the names of several districts within the city, including Yorkville, East York, North York, and York the last three being suburbs that were formally amalgamated into the "megacity" of Toronto on January 1, 1998.

Old Toronto is the part of Toronto, Ontario, Canada, that corresponds to the boundaries of the City of Toronto prior to 1998. It was incorporated as a city in 1834, after being known as the town of York, and being part of York County. Toronto periodically grew in size by annexing adjacent land and municipalities.

In 1954, the City of Toronto and the surrounding suburban towns and townships of York County were joined in a federation known as the Municipality of Metropolitan Toronto (Metro). Later, the lower-tier city annexed two towns until it reached its final boundaries in 1967. In 1998, the municipalities of Metro Toronto were amalgamated into the present-day single-tier City of Toronto, which continues legally from the predecessor City of Toronto, although the by-laws of each municipality remained in force.

Lieutenant-General John Graves Simcoe (25 February 1752 – 26 October 1806) was a British army officer, politician, and colonial administrator who served as the lieutenant governor of Upper Canada from 1791 until 1796. He founded York, which is now known as Toronto, and was instrumental in introducing institutions such as courts of law, trial by jury, English common law, freehold land tenure, and also in the abolition of slavery in Upper Canada.

His long-term goal was the development of Upper Canada (Ontario) as a model community built on aristocratic and conservative principles, designed to demonstrate the superiority of those principles to the republicanism of the United States. His energetic efforts were only partially successful in establishing a local gentry, a thriving Church of England, and an anti-American coalition with select indigenous nations. He is seen by many Canadians as a founding figure in Canadian history, especially by those in Southern Ontario. He is commemorated in Toronto with Simcoe Day.

The Don River is a watercourse in southern Ontario that empties into Lake Ontario, at Toronto Harbour. Its mouth was just east of the street grid of the town of York, Upper Canada, the municipality that evolved into Toronto, Ontario. The Don is one of the major watercourses draining Toronto (along with the Humber, and Rouge Rivers) that have headwaters in the Oak Ridges Moraine.

The Don is formed from two rivers, the East and West Branches, that meet about 7 kilometres (4 mi) north of Lake Ontario while flowing southward into the lake. The area below the confluence is known as the "lower Don", and the areas above as the "upper Don". The Don is also joined at the confluence by a third major branch, Taylor-Massey Creek. The Toronto and Region Conservation Authority (TRCA) is responsible for managing the river and its surrounding watershed.