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