The current street route follows a trail originally cut through the woods by Governor John Graves Simcoe to his summer house on the Don River, Castle Frank.

Named after legislative buildings later burned to the ground by invading American forces, Parliament Street has been a setting for growth and change for more than 200 years.

Shaped by a combination of natural features (Lake Ontario and the Don River Valley) and the built environment (Corktown, Cabbagetown and Regent Park), Parliament Street is a reflection not only of the history of Toronto but of Canada as well.

The fires and the “marshy” air by the lake (which was thought to be unhealthy) influenced the relocation of the parliament buildings, although the name of the street remains to this day.

The Eclipse Theatre, the Winchester Hotel and clothier Harry Rosen offered entertainment, lodging, and clothing to the area's residents.

Grocery, hardware and jewelry stores, restaurants and barbershops served the community, making it a thriving part of Toronto.

New businesses and attractions (from the Distillery District to the 69-acre (28 ha) revitalization of Regent Park) and restorations such as the Toronto Police, 51 Division (West Gas Purifying House, 1899) and the Winchester Hotel (formerly Lakeview Hotel, 1888) have given the community a sense that Parliament Street is returning to its historical roots as an area of intersecting residential, commercial and cultural significance.

North of the Gardiner Expressway, Parliament marks the eastern border of the St. Lawrence neighbourhood, a former industrial area that has been redeveloped as mixed-income and mixed-use community following the precepts of Jane Jacobs.

North of Wellesley and west of Parliament is St. James Town a cluster of apartment towers which is the highest-density neighbourhood in Canada.