JumpStart Preschool (1999) 

I had no interest in any of the JumpStart Preschool games, due to the fact that I never owned one as a kid, but I had some interest in this one because of the train, so without further ado, the JumpStart Preschool all new '99 version featuring the magical train.
JumpStart Preschool is a game released in 1999 that focuses on a preschool curriculum. It serves as an updated version of JumpStart Preschool (1995), and would later be superseded by JumpStart Advanced Preschool. It is also known as Jump Ahead Preschool 2000.
In the game, the player can explore and play in an interactive schoolhouse which contains many activities in the classroom. The player is rewarded with train tickets for completing activities. When the player collects four train tickets, they can go on a magical train ride to one of ten different locations. After visiting a location, the player gets a stamp in their passport book.