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Note that unlike many other large cities, Winnipeg does not have an ideal route through it, such as a freeway. The TransCanada #1 highway utilizes several streets going through Winnipeg's downtown core to cross the city, which is very inefficient if one does not want to spend an hour or two in slow, and congested traffic. You are best off hitching along the shoulder of the Perimeter Highway which encircles Winnipeg. Either the upper half (#101 highway) or the lower half (#100 highway) can be taken, but the lower half is a shorter and more popular route, and also registers as a TransCanada highway. Look for overpasses before you reach the city from the East or West with signs directing you towards the perimeter routes, or ask your driver to drop you off at the Perimeter.

If you're at the centre of the city, take the 21 St. Charles bus West to the outskirts of town. Walk past the Perimeter Hwy overpass and there's a good spot across from the Chapel Lawm Memorial Gardens. There's a stoplight and a Tim Hortons, plenty of slow traffic and a nice wide shoulder.