One way to make streets more friendly to pedestrians at night is to incorporate pedestrian-scale streetlights over the sidewalk. The Harbord BIA has recently sponsored the installation of such lights along Harbord west of Spadina.
Of course, once upon a time there was no street lighting at all. We easily forget how pervasive street lighting is in the city, and it’s hard to imagine what a street was like without any lighting at all. However, you can get some idea of what it was like by walking along Palmerston south of Harbord at night. For some reason, the special globular street lights are not working, and have not been repaired for ages. The effect is kind of enchanting.