Trent River (Ontario) in the context of Bay of Quinte

York was a town and the second capital of the colony of Upper Canada. It is the predecessor to the old city of Toronto (1834–1998). It was established in 1793 by Lieutenant-Governor John Graves Simcoe as a "temporary" location for the capital of Upper Canada, while he made plans to build a capital near today's London, Ontario. Simcoe renamed the location York after Prince Frederick, Duke of York and Albany, George III's second son. Simcoe gave up his plan to build a capital at London, and York became the permanent capital of Upper Canada on February 1, 1796. That year Simcoe returned to Britain and was temporarily replaced by Peter Russell.

The original townsite was a compact ten blocks near the mouth of the Don River and a garrison was built at the channel to Toronto Harbour. Government buildings and a law court were established. Yonge Street was built, connecting York to the Holland River to the north. To the east, Kingston Road was built to the mouth of the Trent River. In 1797, the town site was expanded to the west to allow for public buildings and expansion. One of the new area's public functions, a public market, was started in 1803. It continues today as St. Lawrence Market.

The Trent–Severn Waterway is a 386-kilometre-long (240 mi) canal route connecting Lake Ontario at Trenton to Georgian Bay, Lake Huron, at Port Severn. Its major natural waterways include the Trent River, Otonabee River, Kawartha Lakes, Lake Simcoe, Lake Couchiching and Severn River. Its scenic, meandering route has been called "one of the finest interconnected systems of navigation in the world".

The canal was surveyed as a military route, but the first lock was built in 1833 as a commercial venture. This connected a number of lakes and rivers near the centre of the waterway, opening a large area to navigation by steamship. The government had begun construction of three additional locks when the Upper Canada Rebellion of 1837 broke out. This led the government to re-examine the project, concluding that the route would have too many locks to allow rapid movement for military purposes. They decided that the locks under construction would be completed, but the rest could be turned into timber slides. This left the completed inland section with no outlet, which business interests addressed by connecting to the route with a number of new toll roads, plank roads, and later, railways.