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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.
=== East towards [[Ontario]] ([[Kenora]] / [[Thunder Bay]] / [[Sault Ste Marie]] / [[Sudbury]] / [[Toronto]])===
Getting East out of Winnipeg is easy breezy Canadian hitching. Start hitchhiking about ~10 minutes walk East of Lagimodiere Blvd. & Fermor Ave.