Heres something interesting. I have been doing some research on the development of the central mountain area. I spent the better part of the day at McMaster Library - specifically: http://library.mcmaster.ca/maps/airphotos/Home.htm What an amazing resource! Aerial photos as far back as...

On today's view, if you follow the rail line/trail that runs perpendicular to those supports in a straight line through the warehouses and hwy. 20/Centennial Pkwy interchange you'll find another segment that meets up with the main rail line. At one time (1938-mid1970s) the QEW-HWY interchange...

Looks like this 1915 Map confirms that John St. was once a mountain access.

Not sure about that but while looking around I found these pictures of the James St. Incline railway (1892-1932)and the old high level reservoir. The reservoir walls still exists and some kind of Scouts building is inside it. The ruins of the Mountain View Hotel have been incorporated...

It certainly does appear that that trail/road did, at one time, connect the top of John St. with Upper James Street. The Clarence Access and this road met near the top. Photos are from 1934 and 1960. It appears to still be connected in the 60's.

It's a pedestrian underpass.