This study analyzes the effects of gender stereotypes on women gubernatorial candidates in the post "Year of the Woman" era to determine whether or not the electoral gains made by women running for legislative office in 1992 also extended to women contesting executive elections in subsequent years. This study proceeds in two parts. The first part of this study provides an empirical analysis of contextual and candidate specific factors thought to affect the way in which gender stereotypes surface during gubernatorial campaigns and how they affect women candidates accordingly. The contextual factors include state culture, party dominance, and tradition of electing women in each state. Candidate specific factors include prior campaign and or office holding experience. The second part of this study adopts a case study approach and focuses on two gubernatorial elections – New Jersey and Virginia – to provide a more detailed examination of how gender stereotypes emerge when women are candidates for governor. The findings from the empirical analysis show that women are more likely to contest gubernatorial elections that are Democratic in their partisanship and non-traditionalist in their political culture. However, these variables did not explain whether women were successful in winning gubernatorial elections. The second part of the analysis expanded on these findings by examining the dominant role gender stereotypes played in a traditionalistic state (Virginia) and the minimal role they played in a non-traditionalistic state (New Jersey). Generalizations were made based on the findings that indicate the importance of the campaign in light of contextual factors and how this affects women candidates in executive elections. Recommendations for a future research agenda regarding elections in which women are candidates for various levels of office are also discussed.