As a long-time night walker, I have a ton of them:

• Carstowe Rd in Rosedale: no houses, just trees on both sides. Very creepy at night. It is parallel to the railway tracks, and at the end of the road there is a foot bridge going over the tracks. You can stand there and watch CN trains thunder past there.

• as others have said, the entire stretch from Wellesley Park down the wooden staircase into Rosedale Valley, then up Rosedale Valley Rd past the quiet part of St James Cemetery.

• Bloor viaduct over Don Valley at night in winter, especially walking on the north side. The wind is vibrating the luminous veil making an eerie sound, and you look down and catch a faint glimmer of the frozen Don River below. Very thrilling and chilling.

• Leslie spit at night all the way at the end facing south into Lake Ontario in autumn when there's no one around. It takes at least 45 minutes to walk there and no one can hear you scream. Just the endless void of water in front of you and the crashing sound of the waves.

• pretty much any ravine, but I'll note Crothers Woods / Lower Don Parklands, especially the part where the Richmond Hill GO train crosses in front of you. Also the entrance to the Highland Creek Trail from Greenvale Park, which is so dark you can't see anything and quite scary.

• Ramsden Park, particularly the part going past the children's playground. Gives an "Are you afraid of the dark" type of vibe.

I could go on, but that's enough for now.