It runs in the north–south direction along the ravine landscape created by Taddle Creek, once a natural waterway that was buried during the Industrial Age and is now flowing underground.

Philosopher Ted Honderich described the walk from his experience as a student [The University of Toronto] was in the middle of the city and had good Victorian buildings, and also such necessary pieces of tradition as a Philosopher's Walk, which led out towards an old village enclosed by the growth of Toronto.

[1] The Alexandra Gates at the northern entrance to the path were constructed at the corner of Bloor Street and Avenue Road in 1901, at the instigation of the Imperial Order of the Daughters of the Empire, and to commemorate the visit of Prince George, Duke of Cornwall (later King George V), and Mary, Duchess of Cornwall (later Queen Mary), that year.

The letters on each post — E and A — stand for Edward and Alexandra, the reigning King and Queen at the time.

When Avenue Road was widened in 1960, the gates were moved to the head of Philosopher's Walk.