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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. Alternatively (and significantly faster and safer), you could take the GO train from Union Station to Oshawa GO and then transfer to the 90 - Newcastle Bus. Go to the very end of the bus route and walk 15 minutes east to the outskirts of the city. There are plenty of houses that have driveways that cars can pull over in and pick you up.

Others advise to avoid hitching within city limits, as it is an approach sometimes used by prostitutes to acquire customers. If you prefer, you may take transit to one of the smaller centres outside of the city. GO transit (www.gotransit.ca) has regular trains leaving Union station downtown Toronto for Oshawa (60km). Get off at the Oshawa train station, there are on-ramps onto the 401 nearby (20 mins unpleasant walk). Oshawa also has it's own public transit system that can get you further east. Have a sign for points east, as there is a lot of local traffic in the Oshawa area. Alternatively, from Oshawa, you can get aboard a GO bus for Peterborough (80km), or a ride VIA rail into Cobourg (117km). Both of these cities are well out of the GTA and are easier to walk to good hitching points. Onramps onto the 401 in Cobourg are good spots, and if you find yourself in Peterborough, the junction of HWY 115 and Lansdowne st, where HWY 7 begins, is a good place to begin travels towards Ottawa. Highway 7 between Peterborough and Ottawa is notorious for being a bit tough to hitch on, though I personally have never had difficulties on it.