go a bit north of the downtown core and check out the schools n such, i live in newmarket theres quite a few.
ive always wanted to hit up the rails around the steamwhistle brewery, thats right by the cn tower/rogers center, they definately look doable, they also have like 20 of picnic tables just kinda chillin there in a corner, they put them away for the winter, theres not a problem with security there i ride my bike there all the time and people tend to just stop and watch and then keep going, its pretty sweet
ya man that warden rail is so intense, that would a sick urby, there plenty in scarb area. Mid scarborough also has some sweet ones, its right beside kennedy station. plenty around all about finding them.
you have to realize eastern toronto isnt toronto, from port union or morningside out in east scarborough the shwa is like 15-20 minutes, anytime anyone refers to toronto i always assume the area within a 10 minute drive from the downtown core.
glenview middle school has some fresh urbs, especially around back where theres this big hill thing. you could pprobably even set up your own urban or something if you had a piece of metal tubing or PVC tubing.