A ‘generation’ is an identifiable group sharing birth years and significant life events at critical developmental ages. There is a paucity of literature examining how parental cognitions and lifestyle behaviors differ by generation and whether generational differences are substantial enough to warrant consideration during the development of health interventions. This study compared generational differences in weight-related cognitions and lifestyle behaviors of mothers of young children who were categorized as Generation X (born 1965–1981, n = 158) and Generation Y (aka Millennials; born 1982–1999, n = 162). Survey results indicated that Generation X had significantly higher family affluence; thus, this was controlled in subsequent analyses. Analysis of covariance indicated that Millennials had more positive expectations about the benefits of engaging in healthy eating and physical activity than comparators, but not significantly so. Millennial mothers placed significantly higher value on physical activity for themselves than Generation X mothers, but both generations were neutral on the value of personal physical activity. No generational differences were noted in self-efficacy of mothers for promoting childhood obesity-prevention practices to children and self-efficacy for personally engaging in weight-protective behaviors. Millennial mothers had significantly more family meals/week, however generations did not differ on the value placed on family meals, where family meals were eaten, or whether media devices were used at mealtime. Few differences were noted between the generations for most child feeding behaviors, except that Millennials reported placing significantly less pressure on children to eat. Mothers’ modeling of weight-related behaviors as a means for children’s observational learning about healthy eating, physical activity, and sedentary behaviors did not differ by generational group. The eating behaviors of mothers differed little between generations. Millennial mothers allowed significantly more media devices in children’s bedrooms and personally engaged in more screen time daily than comparators. Overall, the two generational groups were more similar than different in weight-related cognitions as well as for personal and parenting lifestyle behaviors. The results suggest that tailoring interventions for individuals at a similar life-stage (e.g., mothers of young children) by generation may not be warranted.