An expanded game of JumpStart 1st Grade
JumpStart 1st Grade is a grade-based JumpStart game released by Knowledge Adventure in 1999. It teaches a 1st grade curriculum. It is an updated version of JumpStart 1st Grade (1995), and would later be replaced by JumpStart Advanced 1st Grade. In the game, the player helps Frankie the dog find treasures by completing activities around the school.
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I think this is the one I had as a kid but there was this painting mini game thing with stamps and it was so fun.