One in four Canadian adults is obese, and more women are entering pregnancy with a higher body mass index (BMI) than in the past. Pregnant women who are overweight or obese have a higher risk of pregnancy-related complications than women of normal weight. Gestational weight gain (GWG) is also associated with childhood obesity. Although the factors influencing weight gain during pregnancy are multifaceted, little is known about the social inequality of GWG. This review will address some of the socioeconomic factors and maternal characteristics influencing weight gain and the impact that excessive GWG has on health outcomes such as post-partum weight retention. The effects of an overweight or obese pre-pregnancy BMI on GWG and neonatal outcomes will also be addressed. The timing of weight gain is also important, as recommendations now include trimester-specific guidelines. While not conclusive, preliminary evidence suggests that excessive weight gain during the first trimester is most detrimental.