There are several routes that you can take, including the Trans-Canada Highway (Highway 1) and the Yellowhead Highway (Highway 16). The Trans-Canada Highway is the most direct route, but it can be busy with truck traffic. The Yellowhead Highway is a more scenic route, but it is longer and can be more challenging to drive in winter weather.
By train, the trip from Oshawa to Winnipeg takes around 24 hours. There is one direct train per day, operated by VIA Rail. The train departs from Oshawa Station and arrives at Winnipeg Union Station.
By plane, the flight from Oshawa to Winnipeg takes around 3 hours and 30 minutes. There are direct flights available from Toronto Pearson International Airport (YYZ) to Winnipeg James Armstrong Richardson International Airport (YWG).