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0:00 Crosscountry Canada - 1986
5:00 Crosscountry Canada Platinum - 2000
10:04 Crosscountry Canada 2 - 2002

More about Crosscountry Canada (from Wikipedia):

Crosscountry is an educational simulation software series of programs for North American students (grade one through grade nine). Many schools use these games as a fun way to teach their students about the states, provinces, territories, and cities. The game is published by Ingenuity Works, a Vancouver-based company originally known as Didatech Software.

In most of the games, the player will drive an 18-wheeler to pick up and deliver commodities to the cities assigned, while making decisions about the best route, when to eat, sleep, fill up gas, etc. In the game series, the player will play as a truck driver where they will make the most money if beneficial decisions are made during their assignment.

Crosscountry Canada (1986)
This was the second game in the series, released in 1986 for the Apple II by Didatech Software, and later ported to DOS in 1991. It was also ported to the ICON, the made-in-Canada educational computer platform. Home of the Underdogs deemed Crosscountry Canada "One of the best edutainment titles ever made".
This title has since been made available on several websites, free-to-play.

Crosscountry Canada Platinum (2000)
The game was added to incorporate the new territory of Nunavut and the Confederation Bridge in Prince Edward Island.

Crosscountry Canada 2 (2002)
This game was released in 2002, by Ingenuity Works. Players drive an 18-wheeler truck picking up and delivering commodities across Canada while learning about provinces, cities, territories and more. Making wise decisions along the way will result in a successful trip. It features different large cities throughout Canada, and is an on-rails driving game.