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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 :)
Hitchhiker François Gobert went there end of January 2016 and spent 2 hours on the ramp before being picked... I almost froze! The best solution is to take the train untill Oshawa and start from there! Scarborough is a pain to get out from! People didn't give a shit at all!
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.
