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Some say that hitching out of Toronto is difficult. But as not so many points seem to have been tried yet, maybe you can give it a try and discover some new ones.
Easiest way: Bloor-Danforth subway all the way East to Kennedy, transfer to Scarborough RT, go all the way to McCowan, exit, walk North to Corporate Drive 401 ramp. In fact, on Google street view you can see a hitch hiker there getting picked up :)
To go East, you need to reach Highway 401, North of the city centre. You can reach it via Don Valley Parkway (404), slightly East of the centre. There are several on-ramps to it such as Dundas St and Queen St, a walkable distance from the centre. Please note that you cross a deprived area on your way there (around Moss park), but it's generally safe.