The teams set off from their Pit Stop in eastern Montana and receive a clue telling them to fly to Montreal, Canada and then find the basement of the C.D.P. Capital Building in Montreal's underground city. Next they take part in a Detour --- Slide It (travel 22 miles and participate in the sport of curling) or Roll It (travel 23 miles and then roll four logs along a one-hundred foot course.) The Weavers and Linzes both opt for Slide It while the Bransens opt for Roll It and taxi/plane confusion causes great delays. Next they all travel 26 miles to the American Pavilion, built by Buckminster Fuller, where they climb a steep staircase and find a clue directing them to a door called Porte D. They make their way to the Olympic Park and pull departure times --- Linz - 5:50 A.M., Bransen - 5:45 A.M. and Weaver - 5:55 A.M., but the Weavers nearly quit.
After departing, the teams are flown by charters to a mystery desination --- Toronto, Canada and then travel to La Tour C.N. (the C.N. Tower) where they use binoculars to spot their next clue. A Detour, Ship or Shop requires them to either sail across Toronto Harbor and retrieve a nautical flag, or search among over one-hundred people for one whose foot fits a particular pair of shoes. The Linz and Weaver families opt for Ship while the Bransens choose Shop. The teams cross Niagara Falls to their final destination city and a jigsaw puzzle of Central and North America determines which family crosses the finish line first.