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One hundred and seventeen years ago, between 1841 and 1867, the Overland Trail saw approximately 350,000 Oregon and California bound North Americans traverse its landscape. This westward migration painted the American frontier with a white sea of wagon covers, spotted the grassy plains with brown patches of oxen herds, and lighted the night sky with open cooking fires. Men and women Overlanders experienced this life-changing event in different ways, which are crucial to understanding the dynamics and interaction between these people and their frontier context. Gender-specific roles and social standards of masculinity and femininity carried from emigrants’ previous lives influenced their perception of the Overland Trail, interaction with the environment, and their future on the western frontier. These influences affected the settlers throughout the entire journey, beginning with their decision for such a move.