This study adopts an intergenerational approach to explore parental activities to facilitate children's transition to kindergarten. Structured interviews were conducted with 76 mothers from a diverse community sample whose children were about to start kindergarten. The emotional "valence," or general positivity or negativity, of the mothers' recounted recollections of their own school experiences regarding teachers, peers, and the school involvement of their own parents was coded from the interviews. Findings support an intergenerational trend for the use of academic transition activities. Positive recollections of the school involvement of their own parents were associated with reporting greater engagement in current academic transition activities, even when accounting for present income, self-esteem and self-efficacy. The valence of school recollections did not predict engagement in discussions about the social aspects of the transition to school. (Contains 3 tables.)