The area that presently comprises the Entertainment District is rich in history, having experienced nearly two centuries of continual change in its built character and land uses, including periods of growth and decline.

In the early part of the 19th century, the area was primarily a wealthy residential neighbourhood that housed the Parliament Buildings of Upper Canada.

At the turn of the last century and with the advent of the railroad, the area was a burgeoning industrial and manufacturing district that included primarily poor and working class housing where many immigrants to Toronto settled.

By the middle of the last century, the garment industry had risen and begun to fall, and the area entered into an era of economic decline fuelled by suburbanization combined with a diminishing manufacturing sector.

Towards the end of the last century, the area began to experience an emergence with the influx of entertainment, creative and IT industries, and aided by innovative planning policies that encouraged mixed uses and the adaptive reuse of former warehouses.

Benefiting from economic, environmental, and social factors driving downtown growth, the present-day Entertainment District is in the midst of a renaissance, firmly establishing itself as a thriving and vibrant district for living, creating, working, and playing.