Two towers being built as part of CIBC Square will be linked to the Path system, extending it to the east to cross over Yonge Street by a pedestrian bridge into the Backstage Condominium building (Esplanade and Yonge corner), giving closed access to Union Station, Scotiabank Arena, and other buildings in Toronto's Financial District.

Toronto's downtown sidewalks were overcrowded, and new office towers were removing the much-needed small businesses from the streets.

The designers of the Toronto-Dominion Centre, the first of Toronto's major urban developments in the 1960s (completed in 1967), were the first to include underground shopping in their complex, with the possibility of future expansion built in.

Construction of the Path tunnel north from Scotia Plaza through the Bay Adelaide Centre started in the fourth quarter of 2007.

[6] In August 2014, a major southward expansion of the Path network brought it closer to the Toronto waterfront, with the opening of a covered pedestrian bridge connecting Scotiabank Arena south to RBC WaterPark Place on Queens Quay (crossing the Lake Shore Boulevard / Gardiner Expressway corridor and Harbour Street).

[9] In early November 2020, a connection was opened between the Maple Leaf Square complex (via the basement-level Longo's supermarket) and ÏCE Condominiums at York Centre.

[10] On December 5, 2020, the new Union Station Bus Terminal was opened within the new CIBC Square complex and connected via a skywalk to the Scotiabank Arena.

[13] The system facilitates pedestrian linkages to public transit, accommodating more than 200,000 daily commuters and thousands of additional tourists and residents en route to sports and cultural events.

Its underground nature provides pedestrians with a safe haven from the winter cold and snow, as well as relief from the summer heat and humidity.

Within the various buildings, pedestrians can find a Path system map, plus cardinal directions (red for south, orange for west, blue for north, yellow for east) on ceiling signs at selected junctions.