The objective of this study was to determine the preliminary effectiveness of an intervention to mitigate adverse pregnancy outcomes associated with pre-pregnancy obesity in American Samoa. We enrolled n = 80 low-risk pregnant women at <14 weeks' gestation. A complete case analysis was conducted with randomized group assignment (group prenatal care-delivered intervention vs. one-on-one usual care) as the independent variable. Primary outcomes were gestational weight gain and postpartum weight change. Secondary outcomes included gestational diabetes screening and exclusive breastfeeding at 6 weeks post partum. Other outcomes reported include gestational diabetes incidence, preterm birth, mode of birth, infant birth weight, and macrosomia. Gestational weight gain was lower among group versus usual care participants (mean [SD], 9.46 [7.24] kg vs. 14.40 [8.23] kg; p = 0.10); postpartum weight change did not differ between groups. Although the proportion of women who received adequate gestational diabetes screening (78.4% group; 65.6% usual care) was similar, there were clinically important between-group differences in exclusive breastfeeding (44.4% group; 25% usual care), incidence of gestational diabetes (27.3% group; 40.0% usual care), and macrosomia (8.3% group; 29.0% usual care). It may be possible to address multiple risk factors related to intergenerational transmission of obesity in this high-risk setting using a group care-delivered intervention.