Curiously, this stretch of path is all that remains of part of the north end of "old" Riverside Drive. Consider this aerial comparison. In the upper image (2019) i've drawn a yellow oval around that part of the woods where the path runs.
The lower image (1928) shows what was then Riverside Drive (then just a dirt road) running to the east of the old Hurdman farmstead.
Here's the Old Riverside Drive (yellow arrows) on a 1906 top map (detail.) In fact, this roadway appears at least as far back as H. F. Walling's 1863 map of the area.
The now-overgrown section of Riverside Drive was cut off from traffic when the Queensway bridge was opened in the 1960s. The section south of Hurdman Station was repurposed as bus transitway.

